930-30-3,MFCD00001401
Catalog No.:AA00IHDE

930-30-3 | 2-Cyclopenten-1-one

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1g
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$13.00   $9.00
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5g
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$22.00   $16.00
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10g
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$28.00   $19.00
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25g
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$65.00   $45.00
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100g
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250g
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  • Technical Information
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Technical Information
Catalog Number:
AA00IHDE
Chemical Name:
2-Cyclopenten-1-one
CAS Number:
930-30-3
Molecular Formula:
C5H6O
Molecular Weight:
82.1005
MDL Number:
MFCD00001401
SMILES:
C1CC(=O)C=C1
NSC Number:
73117
Properties
Properties
 
BP:
136°C at 760 mmHg  
Form:
Liquid  
Refractive Index:
n20/D 1.481(lit.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
92.1  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
0  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
0.5  

Literature

Title: Prostaglandin D2 toxicity in primary neurons is mediated through its bioactive cyclopentenone metabolites.

Journal: Neurotoxicology 20131201

Title: Fragrance material review on 3-methyl-2-(pentyloxy)-2-cyclopenten-1-one.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20121001

Title: Ab initio calculations of molecular properties of low-lying electronic states of 2-cyclopenten-1-one--link with biological activity.

Journal: Journal of molecular modeling 20121001

Title: Asymmetric Brønsted acid-catalyzed nazarov cyclization of acyclic α-alkoxy dienones.

Journal: Chemistry, an Asian journal 20121001

Title: 11-(4-Methyl-phen-yl)-8,9-dihydro-7H-benzo[f]cyclo-penta-[b]quinolin-10(11H)-one.

Journal: Acta crystallographica. Section E, Structure reports online 20120901

Title: Selective 'one-pot' synthesis of functionalized cyclopentenones.

Journal: The Journal of organic chemistry 20120720

Title: Diastereoselective [4 + 1] cycloaddition of alkenyl propargyl acetates with CO catalyzed by [RhCl(CO)2]2.

Journal: The Journal of organic chemistry 20120720

Title: Tetramethylnorbornadiene, a versatile alkene for cyclopentenone synthesis through intermolecular Pauson-Khand reactions.

Journal: Organic letters 20120706

Title: Sinularones A-I, new cyclopentenone and butenolide derivatives from a marine soft coral Sinularia sp. and their antifouling activity.

Journal: Marine drugs 20120601

Title: Oxazolidinone-promoted, torquoselective Nazarov cyclizations.

Journal: Organic letters 20120406

Title: Regioselective cleavage of 22-oxo-23-spiroketals. Novel cholestanic frameworks with pyranone and cyclopentenone E rings on the side chain.

Journal: Steroids 20120401

Title: Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones.

Journal: Organic letters 20120316

Title: Unimolecular thermal decomposition of phenol and d5-phenol: direct observation of cyclopentadiene formation via cyclohexadienone.

Journal: The Journal of chemical physics 20120128

Title: Regio- and stereoselective synthesis of cyclopentenones: intermolecular pseudo-Pauson-Khand cyclization.

Journal: Angewandte Chemie (International ed. in English) 20120102

Title: Δ12-prostaglandin J3, an omega-3 fatty acid-derived metabolite, selectively ablates leukemia stem cells in mice.

Journal: Blood 20111222

Title: Formal homo-Nazarov and other cyclization reactions of activated cyclopropanes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20111216

Title: Synthetic molecular mimics of naturally occurring cyclopentenones exhibit antifungal activity towards pathogenic fungi.

Journal: Microbiology (Reading, England) 20111201

Title: Dehydro-leucodin: a guaiane-type sesquiterpene lactone.

Journal: Acta crystallographica. Section E, Structure reports online 20111201

Title: Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Journal: Angewandte Chemie (International ed. in English) 20111111

Title: 7-(3-Nitro-phen-yl)-9,10-dihydro-7H-benzo[h]cyclo-penta-[b]quinolin-8(11H)-one.

Journal: Acta crystallographica. Section E, Structure reports online 20111101

Title: Proteomic studies on protein modification by cyclopentenone prostaglandins: expanding our view on electrophile actions.

Journal: Journal of proteomics 20111019

Title: Cyclopenicillone, a unique cyclopentenone from the cultures of Penicillium decumbens.

Journal: Chemical communications (Cambridge, England) 20111007

Title: Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes.

Journal: Journal of the American Chemical Society 20110928

Title: TFP as a ligand in Au(I)-catalyzed dihydropyran synthesis. Unprecedented rearrangement of dihydropyrans into cyclopentenones.

Journal: Chemical communications (Cambridge, England) 20110907

Title: Dynamic NMR and computational study of 5,5-dimethyl-3,4-di-p-tolyl-2-cylopenten-1-one.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20110901

Title: Enantioselective synthesis of the C10-C20 fragment of fusicoccin A.

Journal: The Journal of organic chemistry 20110819

Title: Regiochemistry in cobalt-mediated intermolecular Pauson-Khand reactions of unsymmetrical internal heteroaromatic alkynes with norbornene.

Journal: The Journal of organic chemistry 20110701

Title: Kraft mill effluent survey: progress toward best management practices for reducing effects on fish reproduction.

Journal: Environmental toxicology and chemistry 20110601

Title: Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Journal: Journal of the American Chemical Society 20110427

Title: An IMDAF cycloaddition approach toward the synthesis of the lycopodium alkaloid (±)-fawcettidine.

Journal: The Journal of organic chemistry 20110415

Title: Defensive sesterterpenoids with unusual antipodal cyclopentenones from the leaves of Leucosceptrum canum.

Journal: Organic letters 20110401

Title: Enantioselective, biocatalytic reduction of 3-substituted cyclopentenones: application to the asymmetric synthesis of an hNK-1 receptor antagonist.

Journal: Organic letters 20110304

Title: Thiol-activated DNA damage by α-bromo-2-cyclopentenone.

Journal: Chemical research in toxicology 20110218

Title: Omega-3 fatty acid oxidation products prevent vascular endothelial cell activation by coplanar polychlorinated biphenyls.

Journal: Toxicology and applied pharmacology 20110215

Title: Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Journal: Organic letters 20110204

Title: Nitro-fatty acids and cyclopentenone prostaglandins share strategies to activate the Keap1-Nrf2 system: a study using green fluorescent protein transgenic zebrafish.

Journal: Genes to cells : devoted to molecular & cellular mechanisms 20110101

Title: The C-terminus of H-Ras as a target for the covalent binding of reactive compounds modulating Ras-dependent pathways.

Journal: PloS one 20110101

Title: Sprouty2 and Spred1-2 proteins inhibit the activation of the ERK pathway elicited by cyclopentenone prostanoids.

Journal: PloS one 20110101

Title: Effluent monitoring at a bleached kraft mill: directions for best management practices for eliminating effects on fish reproduction.

Journal: Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering 20110101

Title: Palmaenones A and B, two new antimicrobial chlorinated cyclopentenones from discomycete Lachnum palmae.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Characterization, synthesis and self-aggregation of (-)-alternarlactam: a new fungal cytotoxin with cyclopentenone and isoquinolinone scaffolds.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20101227

Title: The moss Physcomitrella patens contains cyclopentenones but no jasmonates: mutations in allene oxide cyclase lead to reduced fertility and altered sporophyte morphology.

Journal: The New phytologist 20101101

Title: Chemical constituents from Aphanamixis grandifolia.

Journal: Chemical & pharmaceutical bulletin 20101101

Title: Cyclopentenone prostaglandins with dienone structure promote cross-linking of the chemoresistance-inducing enzyme glutathione transferase P1-1.

Journal: Molecular pharmacology 20101001

Title: Stereochemical and skeletal diversity arising from amino propargylic alcohols.

Journal: Organic letters 20100618

Title: A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.

Journal: European journal of medicinal chemistry 20100601

Title: Detoxification without intoxication: herbicide safeners activate plant defense gene expression.

Journal: Plant physiology 20100501

Title: Chemical and biochemical study of industrially produced San Simón da Costa smoked semi-hard cow's milk cheeses: Effects of storage under vacuum and different modified atmospheres.

Journal: Journal of dairy science 20100501

Title: Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.

Journal: Organic letters 20100416

Title: Alteration of biochemical and pathological properties of TDP-43 protein by a lipid mediator, 15-deoxy-Delta(12,14)-prostaglandin J(2).

Journal: Experimental neurology 20100401

Title: Trichoderone, a novel cytotoxic cyclopentenone and cholesta-7, 22-diene-3 beta, 5 alpha, 6 beta-triol, with new activities from the marine-derived fungus Trichoderma sp.

Journal: Journal of industrial microbiology & biotechnology 20100301

Title: Benzylidene cyclopentenediones: First irreversible inhibitors against botulinum neurotoxin A's zinc endopeptidase.

Journal: Bioorganic & medicinal chemistry letters 20100101

Title: Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition.

Journal: Marine drugs 20091201

Title: Isolation of C11 cyclopentenones from two didemnid species, Lissoclinum sp. and Diplosoma sp.

Journal: Marine drugs 20091201

Title: Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

Journal: The Journal of organic chemistry 20091106

Title: Asymmetric intermolecular Pauson-Khand reaction of symmetrically substituted alkynes.

Journal: Organic letters 20091001

Title: Effects of 15-deoxy-delta 12, 14-prostaglandin J2 on the expression of p53 in MCF-7 cells.

Journal: Annals of the New York Academy of Sciences 20090801

Title: Use of MEKC for the analysis of reactant and product of Baylis-Hillman reaction.

Journal: Journal of separation science 20090501

Title: Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts.

Journal: Chemical research in toxicology 20090501

Title: Selective, potent PPARgamma agonists with cyclopentenone core structure.

Journal: Bioorganic & medicinal chemistry letters 20090401

Title: Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.

Journal: Organic letters 20090219

Title: Asymmetric C2-C3 cyclopentannulation of the indole ring.

Journal: Journal of the American Chemical Society 20090218

Title: Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones.

Journal: Organic & biomolecular chemistry 20090121

Title: Au(I)-catalyzed hydrative rearrangement of 1,1-diethynylcarbinol acetates to functionalized cyclopentenones and allenones.

Journal: The Journal of organic chemistry 20090102

Title: Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones.

Journal: Organic letters 20090101

Title: New cyclopentenones from strain Trichoderma sp. YLF-3.

Journal: Natural product research 20090101

Title: The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-gamma ligands.

Journal: Organic & biomolecular chemistry 20081221

Title: Impact of cyclopentenone-oxylipins on the proteome of Arabidopsis thaliana.

Journal: Biochimica et biophysica acta 20081201

Title: Gold-catalyzed hydrative carbocyclization of 1,5- and 1,6-diyn-3-ones via an oxygen transfer process.

Journal: The Journal of organic chemistry 20081107

Title: Synthesis of fluoroneplanocin A.

Journal: Current protocols in nucleic acid chemistry 20080901

Title: Co-complexes derived from alkene insertion to alkyne-dicobaltpentacarbonyl complexes: insight into the regioselectivity of pauson-khand reactions of cyclopropenes.

Journal: The Journal of organic chemistry 20080815

Title: Highly enantioselective [4 + 2] cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation.

Journal: Organic letters 20080807

Title: Effect of cyclopentanone prostaglandin 15-deoxy-delta12,14PGJ2 on early functional recovery from experimental spinal cord injury.

Journal: Shock (Augusta, Ga.) 20080801

Title: Electrophilic cyclopentenone neuroprostanes are anti-inflammatory mediators formed from the peroxidation of the omega-3 polyunsaturated fatty acid docosahexaenoic acid.

Journal: The Journal of biological chemistry 20080718

Title: Synthesis of cyclopentenones via intramolecular HWE and the palladium-catalyzed reactions of allylic hydroxy phosphonate derivatives.

Journal: The Journal of organic chemistry 20080718

Title: Matrix isolation studies of photochemical and thermal reactions of 3- and 5-membered cyclic hydrocarbons with CrCl2O2.

Journal: The journal of physical chemistry. A 20080619

Title: Theoretical elucidation of the rhodium-catalyzed [4 + 2] annulation reactions.

Journal: Journal of computational chemistry 20080415

Title: N-metalated imines by reaction of 1,1-diethoxybut-2-ene with aromatic nitriles, as useful intermediates for the synthesis of substituted pyrimidines and cyclopentenones.

Journal: Chemical communications (Cambridge, England) 20080414

Title: Synthesis and bioorthogonal coupling chemistry of a novel cyclopentenone-containing unnatural tyrosine analogue.

Journal: Bioorganic chemistry 20080401

Title: Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.

Journal: Organic letters 20080320

Title: Pro-apoptotic activity of cyclopentenone in cancer cells.

Journal: Anticancer research 20080101

Title: Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers.

Journal: Angewandte Chemie (International ed. in English) 20080101

Title: Photooxygenation of masked o-benzoquinones: an efficient entry into highly functionalized cyclopentenones from 2-methoxyphenols.

Journal: Angewandte Chemie (International ed. in English) 20080101

Title: A rapid microwell fluorescence immunoassay for cellular protein detection.

Journal: Biological procedures online 20080101

Title: Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes.

Journal: The Journal of organic chemistry 20071221

Title: Detection of a pathway from linoleate to a novel cyclopentenone: cis-12-oxo-10-phytoenoic acid in sunflower roots.

Journal: Chembiochem : a European journal of chemical biology 20071217

Title: Anti-inflammatory lipid mediator 15d-PGJ2 inhibits translation through inactivation of eIF4A.

Journal: The EMBO journal 20071212

Title: A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes.

Journal: Journal of the American Chemical Society 20071121

Title: Endogenous lipid mediators in the resolution of airway inflammation.

Journal: The European respiratory journal 20071101

Title: Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process.

Journal: The Journal of organic chemistry 20071026

Title: Specific subcellular localization of siRNAs delivered by lipoplex in MCF-7 breast cancer cells.

Journal: Biochimie 20071001

Title: 15-Deoxy-delta(12,14)-prostaglandin J(2) down-regulates CXCR4 on carcinoma cells through PPARgamma- and NFkappaB-mediated pathways.

Journal: Experimental cell research 20071001

Title: N-heterocyclic carbene catalyzed aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines.

Journal: The Journal of organic chemistry 20070914

Title: Electrophilic cyclopentenone isoprostanes in neurodegeneration.

Journal: Journal of molecular neuroscience : MN 20070901

Title: Jet-cooled phosphorescence excitation spectrum of the T1(n,pi*) <-- S0 transition of 2-cyclopenten-1-one.

Journal: The journal of physical chemistry. A 20070830

Title: Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate.

Journal: Chemistry and physics of lipids 20070801

Title: Antiinflammatory effects of the cyclopentenone isoprostane 15-A(2)-IsoP in human gestational tissues.

Journal: Free radical biology & medicine 20070615

Title: Bromomyrothenone B and botrytinone, cyclopentenone derivatives from a marine isolate of the fungus botrytis.

Journal: Journal of natural products 20070201

Title: Direct evidence for the covalent modification of glutathione-S-transferase P1-1 by electrophilic prostaglandins: implications for enzyme inactivation and cell survival.

Journal: Archives of biochemistry and biophysics 20070115

Title: Modification of proteins by cyclopentenone prostaglandins is differentially modulated by GSH in vitro.

Journal: Annals of the New York Academy of Sciences 20070101

Title: A catalytic method for converting vinylic furanoses into cyclopentenones.

Journal: Angewandte Chemie (International ed. in English) 20070101

Title: Prostanoids with cyclopentenone structure as tools for the characterization of electrophilic lipid-protein interactomes.

Journal: Annals of the New York Academy of Sciences 20061201

Title: Induction of apoptosis in estrogen receptor-negative breast cancer cells by natural and synthetic cyclopentenones: role of the IkappaB kinase/nuclear factor-kappaB pathway.

Journal: Molecular pharmacology 20061101

Title: Cyclopentenone: a special moiety for anticancer drug design.

Journal: Anti-cancer drugs 20061001

Title: Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic dothideomycete sp. LRUB20.

Journal: Journal of natural products 20060901

Title: Cytoskeleton/endoplasmic reticulum collapse induced by prostaglandin J2 parallels centrosomal deposition of ubiquitinated protein aggregates.

Journal: The Journal of biological chemistry 20060811

Title: Metal-catalyzed chemoselective cycloisomerization of cis-2,4-dien-1-als to 3-cyclopentenones and 4-alkylidene-3,4-dihydro-2H-pyrans.

Journal: Organic letters 20060706

Title: Cyclopentenone isoprostanes are novel bioactive products of lipid oxidation which enhance neurodegeneration.

Journal: Journal of neurochemistry 20060601

Title: Effects of 15-deoxy-Delta12,14-prostaglandin-J2 during hyperdynamic porcine endotoxemia.

Journal: Intensive care medicine 20060501

Title: Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation.

Journal: Angewandte Chemie (International ed. in English) 20060403

Title: Analysis of fungal cyclopentenone derivatives from Hygrophorus spp. by liquid chromatography/electrospray-tandem mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20060301

Title: Reactive lipid species from cyclooxygenase-2 inactivate tumor suppressor LKB1/STK11: cyclopentenone prostaglandins and 4-hydroxy-2-nonenal covalently modify and inhibit the AMP-kinase kinase that modulates cellular energy homeostasis and protein translation.

Journal: The Journal of biological chemistry 20060203

Title: Low expression of MRP1/GS-X pump ATPase in lymphocytes of Walker 256 tumour-bearing rats is associated with cyclopentenone prostaglandin accumulation and cancer immunodeficiency.

Journal: Cell biochemistry and function 20060101

Title: NF-kappaB: a stress-regulated switch for cell survival.

Journal: Antioxidants & redox signaling 20060101

Title: Asymmetric sulfonium ylide mediated cyclopropanation: stereocontrolled synthesis of (+)-LY354740.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20051223

Title: Terpestacin core structure. control of stereochemistry.

Journal: Organic letters 20051027

Title: Differential selectivity of protein modification by the cyclopentenone prostaglandins PGA1 and 15-deoxy-Delta12,14-PGJ2: role of glutathione.

Journal: FEBS letters 20051024

Title: Cyclopentenone isoprostanes inhibit the inflammatory response in macrophages.

Journal: The Journal of biological chemistry 20051021

Title: The cyclopentenone 15-deoxy-delta(12,14)-prostaglandin J2 inhibits G1/S transition and retinoblastoma protein phosphorylation in immortalized lymphocytes from Alzheimer's disease patients.

Journal: Experimental neurology 20051001

Title: New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n + m + p medium-sized lactones: short synthesis of (-)-phoracantholide-J.

Journal: Organic letters 20050915

Title: Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.

Journal: Angewandte Chemie (International ed. in English) 20050912

Title: New cyclopentenone derivatives from an endophytic Streptomyces sp. isolated from the mangrove plant Aegiceras comiculatum.

Journal: The Journal of antibiotics 20050901

Title: An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A.

Journal: The Journal of organic chemistry 20050819

Title: Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes.

Journal: Organic letters 20050804

Title: Phenols, quinolines, indoles, benzene, and 2-cyclopenten-1-ones are oviductal toxicants in cigarette smoke.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20050701

Title: Identification of the major urinary metabolite of the highly reactive cyclopentenone isoprostane 15-A(2t)-isoprostane in vivo.

Journal: The Journal of biological chemistry 20050701

Title: Highlight for phenols, quinolines, indoles, benzene and 2-cyclopenten-1-ones are oviduct toxicants in cigarette smoke, by Prue Talbot, Karen Riveles, and Ryan Rosa: list of tobacco-smoke constituents that are harmful for reproduction grows--passive smokers may be at risk.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20050701

Title: Alpha-hydroxy cyclopentenones from alpha-diketones.

Journal: Organic letters 20050623

Title: Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

Journal: Organic letters 20050623

Title: The intermolecular Pauson-Khand reaction.

Journal: Angewandte Chemie (International ed. in English) 20050513

Title: Peroxisome proliferator-activated receptor-gamma is a new therapeutic target in sepsis and inflammation.

Journal: Shock (Augusta, Ga.) 20050501

Title: 3,3a-Dihydrocyclopenta[b]chromen-1(2H)-ones from the reaction of salicylaldehyde and 2-cyclopenten-1-one.

Journal: Acta crystallographica. Section C, Crystal structure communications 20050501

Title: Cyclopentenone eicosanoids as mediators of neurodegeneration: a pathogenic mechanism of oxidative stress-mediated and cyclooxygenase-mediated neurotoxicity.

Journal: Brain pathology (Zurich, Switzerland) 20050401

Title: Reagent-free Nazarov cyclisations.

Journal: Chemical communications (Cambridge, England) 20050207

Title: Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes.

Journal: Journal of combinatorial chemistry 20050101

Title: The cyclopentenone (A2/J2) isoprostanes--unique, highly reactive products of arachidonate peroxidation.

Journal: Antioxidants & redox signaling 20050101

Title: [Role of prostaglandins in rheumatoid arthritis].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20050101

Title: Inhibition of TNF-alpha promoter activity and synthesis by A11-99-1, a new cyclopentenone from the ascomycete Mollisia melaleuca.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101

Title: Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Effects of cyclopentenone prostaglandins on the expression of heme oxygenase-1 in MCF-7 cells.

Journal: Annals of the New York Academy of Sciences 20041201

Title: Synthesis of 4'-methyl and 4'-cyano carbocyclic 2',3'-didehydro nucleoside analogues via 1,4-addition to substituted cyclopentenones.

Journal: The Journal of organic chemistry 20041126

Title: Protein thiol modification by 15-deoxy-Delta12,14-prostaglandin J2 addition in mesangial cells: role in the inhibition of pro-inflammatory genes.

Journal: Molecular pharmacology 20041101

Title: Targeting of epidermal growth factor receptor by cyclopentenone prostaglandin 15-Deoxy-Delta12,14-prostaglandin J2 in human oral squamous carcinoma cells.

Journal: Cancer letters 20040728

Title: Allenes and transition metals: a diverging approach to heterocycles.

Journal: Organic letters 20040624

Title: Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers.

Journal: Bioorganic & medicinal chemistry 20040615

Title: 15-deoxy-Delta12,14-prostaglandin J2 inhibits glucocorticoid binding and signaling in macrophages through a peroxisome proliferator-activated receptor gamma-independent process.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20040615

Title: Antifungal cyclopentenediones from Piper coruscans.

Journal: Journal of the American Chemical Society 20040609

Title: Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects.

Journal: The Journal of organic chemistry 20040528

Title: Phosphine catalyzed alpha-arylation of enones and enals using hypervalent bismuth reagents: regiospecific enolate arylation via nucleophilic catalysis.

Journal: Journal of the American Chemical Society 20040505

Title: Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using delta-amino beta-ketophosphonates and ring-closing metathesis (RCM).

Journal: Organic letters 20040415

Title: The biphasic effects of cyclopentenone prostaglandins, prostaglandin J(2) and 15-deoxy-Delta(12,14)-prostaglandin J(2) on proliferation and apoptosis in rat basophilic leukemia (RBL-2H3) cells.

Journal: Biochemical pharmacology 20040401

Title: Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes).

Journal: Phytochemistry 20040401

Title: 15d-PGJ2 inhibits oxidized LDL-induced macrophage proliferation by inhibition of GM-CSF production via inactivation of NF-kappaB.

Journal: Biochemical and biophysical research communications 20040213

Title: Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-beta-lactams via Baylis-Hillman or bromoallylation reactions.

Journal: The Journal of organic chemistry 20040206

Title: New Fischer carbene complexes of rhodium(i): preparation and 2-cyclopentenone ring synthesis by annelation to alkynes.

Journal: Journal of the American Chemical Society 20040121

Title: The cyclopentenone product of lipid peroxidation, 15-A2t-isoprostane, is efficiently metabolized by HepG2 cells via conjugation with glutathione.

Journal: Chemical research in toxicology 20040101

Title: An endogenous electrophile that modulates the regulatory mechanism of protein turnover: inhibitory effects of 15-deoxy-Delta 12,14-prostaglandin J2 on proteasome.

Journal: Biochemistry 20031202

Title: Unexpected sensitivity of synthetic Renilla luciferase control vectors to treatment with a cyclopentenone prostaglandin.

Journal: BioTechniques 20031201

Title: Cyclopentenone prostaglandins induce lymphocyte apoptosis by activating the mitochondrial apoptosis pathway independent of external death receptor signaling.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20031115

Title: Practical synthesis of D- and l-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus).

Journal: The Journal of organic chemistry 20031114

Title: Isomerization-cyclization approach to the synthesis of 2-hydroxy-5-alkylidene-cyclopent-2-enones.

Journal: Organic letters 20031030

Title: Urease inhibitory activity of simple alpha,beta-unsaturated ketones.

Journal: Life sciences 20031024

Title: 2-Cyclopenten-1-one and prostaglandin J2 reduce restenosis after balloon angioplasty in rats: role of NF-kappaB.

Journal: FEBS letters 20031009

Title: Structural requirements of cyclopentenone prostaglandins to induce endothelial cell apoptosis.

Journal: Biochemical and biophysical research communications 20030725

Title: The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis.

Journal: Journal of the American Chemical Society 20030716

Title: Thioredoxin as a molecular target of cyclopentenone prostaglandins.

Journal: The Journal of biological chemistry 20030711

Title: Anti-inflammatory activity of 15-deoxy-delta12,14-PGJ2 and 2-cyclopenten-1-one: role of the heat shock response.

Journal: Molecular pharmacology 20030701

Title: Two new cyclopentenone derivatives and a new cyclooctadienone derivative from Erigeron annuus (L.) PERS., Erigeron philadelphicus L., and Erigeron sumatrensis RETZ.

Journal: Chemical & pharmaceutical bulletin 20030701

Title: Chemical synthesis and cytotoxicity of dihydroxylated cyclopentenone analogues of neocarzinostatin chromophore.

Journal: Bioorganic & medicinal chemistry letters 20030616

Title: Role of heme oxygenase-1 protein in the neuroprotective effects of cyclopentenone prostaglandin derivatives under oxidative stress.

Journal: The European journal of neuroscience 20030601

Title: The cyclopentenone-type prostaglandin 15-deoxy-delta 12,14-prostaglandin J2 inhibits CD95 ligand gene expression in T lymphocytes: interference with promoter activation via peroxisome proliferator-activated receptor-gamma-independent mechanisms.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030501

Title: Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones.

Journal: Journal of the American Chemical Society 20030423

Title: The first example of Nazarov reactions of vinyl cumulenyl ketones.

Journal: Organic letters 20030417

Title: Biosynthesis of 14,15-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D(1) pathway.

Journal: Phytochemistry 20030201

Title: Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).

Journal: Bioorganic & medicinal chemistry letters 20030106

Title: Practical synthesis of D-cyclopent-2-enone, the key intermediate of carbocyclic nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: Acyl-lithiation of olefins: formation of cyclopentenones from 1-lithio-butadienes and CO.

Journal: Organic letters 20021226

Title: Role of structure and pH in cyclization of allene oxide fatty acids: implications for the reaction mechanism.

Journal: Chemistry and physics of lipids 20021201

Title: [Cyclopentenone prostaglandin derivatives as neuroprotective compounds].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20021201

Title: Photodimerisation of enones in a clay microenvironment.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20021201

Title: Contribution of covalent protein modification to the antiinflammatory effects of cyclopentenone prostaglandins.

Journal: Annals of the New York Academy of Sciences 20021101

Title: Formation of highly reactive A-ring and J-ring isoprostane-like compounds (A4/J4-neuroprostanes) in vivo from docosahexaenoic acid.

Journal: The Journal of biological chemistry 20020927

Title: The cyclopentenone product of lipid peroxidation, 15-A(2t)-isoprostane (8-isoprostaglandin A(2)), is efficiently conjugated with glutathione by human and rat glutathione transferase A4-4.

Journal: Chemical research in toxicology 20020901

Title: Asymmetric cyclopentannelation: camphor-derived auxiliary.

Journal: Journal of the American Chemical Society 20020828

Title: Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues.

Journal: Bioorganic & medicinal chemistry letters 20020805

Title: Cyclopentenone prostaglandin receptors.

Journal: Prostaglandins & other lipid mediators 20020801

Title: Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones.

Journal: Journal of the American Chemical Society 20020731

Title: Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes.

Journal: Organic letters 20020725

Title: Cobalt-phosphite-catalyzed asymmetric Pauson-Khand reaction.

Journal: The Journal of organic chemistry 20020517

Title: A proinflammatory role for the cyclopentenone prostaglandins at low micromolar concentrations: oxidative stress-induced extracellular signal-regulated kinase activation without NF-kappa B inhibition.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20020515

Title: The cyclopentenone prostaglandin 15-deoxy-Delta(12,14)-prostaglandin J(2) attenuates the development of acute and chronic inflammation.

Journal: Molecular pharmacology 20020501

Title: Epoxyisoprostane and epoxycyclopentenone phospholipids regulate monocyte chemotactic protein-1 and interleukin-8 synthesis. Formation of these oxidized phospholipids in response to interleukin-1beta.

Journal: The Journal of biological chemistry 20020301

Title: A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst.

Journal: Angewandte Chemie (International ed. in English) 20020118

Title: Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of 'cooling' compounds.

Journal: Journal of agricultural and food chemistry 20011101

Title: Highly regio- and stereoselective 1,1-cycloaddition of carbon monoxide with 1,4-dilithio-1,3-dienes. Novel synthetic methods for 3-cyclopenten-1-one derivatives.

Journal: Journal of the American Chemical Society 20011024

Title: Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction.

Journal: The Journal of organic chemistry 20011005

Title: Antiproliferative prostaglandins and the MRP/GS-X pump role in cancer immunosuppression and insight into new strategies in cancer gene therapy.

Journal: Biochemical pharmacology 20011001

Title: Syntheses of D- and L-cyclopentenone derivatives using ring-closing metathesis: versatile intermediates for the synthesis of D- and L-carbocyclic nucleosides.

Journal: The Journal of organic chemistry 20010921

Title: Lewis base effects in the Baylis-Hillman reaction of imines with cyclohex-2-en-1-one and cyclopent-2-en-1-one.

Journal: Chemical communications (Cambridge, England) 20010921

Title: The first reported anionic oxy retro-ene reaction.

Journal: Organic letters 20010920

Title: Determination by enantioselective synthesis of the absolute configuration of CPE, a potential intermediate in coronatine biosynthesis.

Journal: Organic letters 20010920

Title: Multifunctionalized alpha,beta-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: a stereospecific rearrangement initiated by base.

Journal: Carbohydrate research 20010830

Title: Cyclopentenone prostaglandins of the J series inhibit the ubiquitin isopeptidase activity of the proteasome pathway.

Journal: The Journal of biological chemistry 20010810

Title: New bioactive cyclopentenone derivatives as inhibitors of the IL-6 dependent signal transduction.

Journal: The Journal of antibiotics 20010801

Title: Regioselective nucleophilic additions to cross-conjugated dienone system bearing beta-fluorine: a versatile approach to highly substituted 2-cyclopentenones.

Journal: Organic letters 20010726

Title: Discovery of a new efficient chiral ligand for copper-catalyzed enantioselective Michael additions by high-throughput screening of a parallel library.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010618

Title: Explaining photodermatosis: cyclopentenone vs. alpha-methylene-gamma-lactone natural products.

Journal: Fitoterapia 20010601

Title: Cyclopentenone prostaglandins: new insights on biological activities and cellular targets.

Journal: Medicinal research reviews 20010501

Title: Cyclopentenone prostaglandins as potential inducers of intracellular oxidative stress.

Journal: The Journal of biological chemistry 20010413

Title: Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins.

Journal: Journal of neurochemistry 20010401

Title: Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation.

Journal: Journal of leukocyte biology 20010401

Title: Change of the reaction pattern by methodological variations in a multicomponent assembly promoted by Ni complexes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010401

Title: Density functional studies on the Pauson--Khand reaction.

Journal: Journal of the American Chemical Society 20010227

Title: A cyclopentenone prostaglandin activates mesangial MAP kinase independently of PPARgamma.

Journal: Biochemical and biophysical research communications 20010216

Title: Parallel synthesis and biocatalytic amplification of a cross-conjugated cyclopentenone library.

Journal: Journal of combinatorial chemistry 20010101

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Tags:930-30-3 Molecular Formula|930-30-3 MDL|930-30-3 SMILES|930-30-3 2-Cyclopenten-1-one
Catalog No.: AA00IHDE
930-30-3,MFCD00001401
930-30-3 | 2-Cyclopenten-1-one
Pack Size: 1g
Purity: 98%
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$13.00 $9.00
Pack Size: 5g
Purity: 95%
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$22.00 $16.00
Pack Size: 10g
Purity: 98%
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Pack Size: 25g
Purity: 98%
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$65.00 $45.00
Pack Size: 100g
Purity: 98%
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Purity: 98%
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Technical Information
Catalog Number: AA00IHDE
Chemical Name: 2-Cyclopenten-1-one
CAS Number: 930-30-3
Molecular Formula: C5H6O
Molecular Weight: 82.1005
MDL Number: MFCD00001401
SMILES: C1CC(=O)C=C1
NSC Number: 73117
Properties
BP: 136°C at 760 mmHg  
Form: Liquid  
Refractive Index: n20/D 1.481(lit.)  
Storage: Inert atmosphere;2-8℃;  
Complexity: 92.1  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 6  
Hydrogen Bond Acceptor Count: 1  
Hydrogen Bond Donor Count: 0  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 0.5  
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Title: Enantioselective, biocatalytic reduction of 3-substituted cyclopentenones: application to the asymmetric synthesis of an hNK-1 receptor antagonist.

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Title: Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

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Title: Nitro-fatty acids and cyclopentenone prostaglandins share strategies to activate the Keap1-Nrf2 system: a study using green fluorescent protein transgenic zebrafish.

Journal: Genes to cells : devoted to molecular & cellular mechanisms20110101

Title: The C-terminus of H-Ras as a target for the covalent binding of reactive compounds modulating Ras-dependent pathways.

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Journal: PloS one20110101

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Journal: Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering20110101

Title: Palmaenones A and B, two new antimicrobial chlorinated cyclopentenones from discomycete Lachnum palmae.

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Title: Characterization, synthesis and self-aggregation of (-)-alternarlactam: a new fungal cytotoxin with cyclopentenone and isoquinolinone scaffolds.

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Journal: The New phytologist20101101

Title: Chemical constituents from Aphanamixis grandifolia.

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Title: Cyclopentenone prostaglandins with dienone structure promote cross-linking of the chemoresistance-inducing enzyme glutathione transferase P1-1.

Journal: Molecular pharmacology20101001

Title: Stereochemical and skeletal diversity arising from amino propargylic alcohols.

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Title: A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.

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Title: Detoxification without intoxication: herbicide safeners activate plant defense gene expression.

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Title: Chemical and biochemical study of industrially produced San Simón da Costa smoked semi-hard cow's milk cheeses: Effects of storage under vacuum and different modified atmospheres.

Journal: Journal of dairy science20100501

Title: Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.

Journal: Organic letters20100416

Title: Alteration of biochemical and pathological properties of TDP-43 protein by a lipid mediator, 15-deoxy-Delta(12,14)-prostaglandin J(2).

Journal: Experimental neurology20100401

Title: Trichoderone, a novel cytotoxic cyclopentenone and cholesta-7, 22-diene-3 beta, 5 alpha, 6 beta-triol, with new activities from the marine-derived fungus Trichoderma sp.

Journal: Journal of industrial microbiology & biotechnology20100301

Title: Benzylidene cyclopentenediones: First irreversible inhibitors against botulinum neurotoxin A's zinc endopeptidase.

Journal: Bioorganic & medicinal chemistry letters20100101

Title: Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition.

Journal: Marine drugs20091201

Title: Isolation of C11 cyclopentenones from two didemnid species, Lissoclinum sp. and Diplosoma sp.

Journal: Marine drugs20091201

Title: Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

Journal: The Journal of organic chemistry20091106

Title: Asymmetric intermolecular Pauson-Khand reaction of symmetrically substituted alkynes.

Journal: Organic letters20091001

Title: Effects of 15-deoxy-delta 12, 14-prostaglandin J2 on the expression of p53 in MCF-7 cells.

Journal: Annals of the New York Academy of Sciences20090801

Title: Use of MEKC for the analysis of reactant and product of Baylis-Hillman reaction.

Journal: Journal of separation science20090501

Title: Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts.

Journal: Chemical research in toxicology20090501

Title: Selective, potent PPARgamma agonists with cyclopentenone core structure.

Journal: Bioorganic & medicinal chemistry letters20090401

Title: Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.

Journal: Organic letters20090219

Title: Asymmetric C2-C3 cyclopentannulation of the indole ring.

Journal: Journal of the American Chemical Society20090218

Title: Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones.

Journal: Organic & biomolecular chemistry20090121

Title: Au(I)-catalyzed hydrative rearrangement of 1,1-diethynylcarbinol acetates to functionalized cyclopentenones and allenones.

Journal: The Journal of organic chemistry20090102

Title: Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones.

Journal: Organic letters20090101

Title: New cyclopentenones from strain Trichoderma sp. YLF-3.

Journal: Natural product research20090101

Title: The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-gamma ligands.

Journal: Organic & biomolecular chemistry20081221

Title: Impact of cyclopentenone-oxylipins on the proteome of Arabidopsis thaliana.

Journal: Biochimica et biophysica acta20081201

Title: Gold-catalyzed hydrative carbocyclization of 1,5- and 1,6-diyn-3-ones via an oxygen transfer process.

Journal: The Journal of organic chemistry20081107

Title: Synthesis of fluoroneplanocin A.

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Title: Co-complexes derived from alkene insertion to alkyne-dicobaltpentacarbonyl complexes: insight into the regioselectivity of pauson-khand reactions of cyclopropenes.

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Title: Highly enantioselective [4 + 2] cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation.

Journal: Organic letters20080807

Title: Effect of cyclopentanone prostaglandin 15-deoxy-delta12,14PGJ2 on early functional recovery from experimental spinal cord injury.

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Title: Electrophilic cyclopentenone neuroprostanes are anti-inflammatory mediators formed from the peroxidation of the omega-3 polyunsaturated fatty acid docosahexaenoic acid.

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Title: N-metalated imines by reaction of 1,1-diethoxybut-2-ene with aromatic nitriles, as useful intermediates for the synthesis of substituted pyrimidines and cyclopentenones.

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Title: Synthesis and bioorthogonal coupling chemistry of a novel cyclopentenone-containing unnatural tyrosine analogue.

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Title: Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.

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Title: Pro-apoptotic activity of cyclopentenone in cancer cells.

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Title: A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes.

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Title: NF-kappaB: a stress-regulated switch for cell survival.

Journal: Antioxidants & redox signaling20060101

Title: Asymmetric sulfonium ylide mediated cyclopropanation: stereocontrolled synthesis of (+)-LY354740.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20051223

Title: Terpestacin core structure. control of stereochemistry.

Journal: Organic letters20051027

Title: Differential selectivity of protein modification by the cyclopentenone prostaglandins PGA1 and 15-deoxy-Delta12,14-PGJ2: role of glutathione.

Journal: FEBS letters20051024

Title: Cyclopentenone isoprostanes inhibit the inflammatory response in macrophages.

Journal: The Journal of biological chemistry20051021

Title: The cyclopentenone 15-deoxy-delta(12,14)-prostaglandin J2 inhibits G1/S transition and retinoblastoma protein phosphorylation in immortalized lymphocytes from Alzheimer's disease patients.

Journal: Experimental neurology20051001

Title: New silicon-mediated, sequential ring expansions of n-sized 2-cycloalkenones into hydroxyolefinic n + m + p medium-sized lactones: short synthesis of (-)-phoracantholide-J.

Journal: Organic letters20050915

Title: Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.

Journal: Angewandte Chemie (International ed. in English)20050912

Title: New cyclopentenone derivatives from an endophytic Streptomyces sp. isolated from the mangrove plant Aegiceras comiculatum.

Journal: The Journal of antibiotics20050901

Title: An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A.

Journal: The Journal of organic chemistry20050819

Title: Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes.

Journal: Organic letters20050804

Title: Phenols, quinolines, indoles, benzene, and 2-cyclopenten-1-ones are oviductal toxicants in cigarette smoke.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20050701

Title: Identification of the major urinary metabolite of the highly reactive cyclopentenone isoprostane 15-A(2t)-isoprostane in vivo.

Journal: The Journal of biological chemistry20050701

Title: Highlight for phenols, quinolines, indoles, benzene and 2-cyclopenten-1-ones are oviduct toxicants in cigarette smoke, by Prue Talbot, Karen Riveles, and Ryan Rosa: list of tobacco-smoke constituents that are harmful for reproduction grows--passive smokers may be at risk.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20050701

Title: Alpha-hydroxy cyclopentenones from alpha-diketones.

Journal: Organic letters20050623

Title: Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

Journal: Organic letters20050623

Title: The intermolecular Pauson-Khand reaction.

Journal: Angewandte Chemie (International ed. in English)20050513

Title: Peroxisome proliferator-activated receptor-gamma is a new therapeutic target in sepsis and inflammation.

Journal: Shock (Augusta, Ga.)20050501

Title: 3,3a-Dihydrocyclopenta[b]chromen-1(2H)-ones from the reaction of salicylaldehyde and 2-cyclopenten-1-one.

Journal: Acta crystallographica. Section C, Crystal structure communications20050501

Title: Cyclopentenone eicosanoids as mediators of neurodegeneration: a pathogenic mechanism of oxidative stress-mediated and cyclooxygenase-mediated neurotoxicity.

Journal: Brain pathology (Zurich, Switzerland)20050401

Title: Reagent-free Nazarov cyclisations.

Journal: Chemical communications (Cambridge, England)20050207

Title: Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes.

Journal: Journal of combinatorial chemistry20050101

Title: The cyclopentenone (A2/J2) isoprostanes--unique, highly reactive products of arachidonate peroxidation.

Journal: Antioxidants & redox signaling20050101

Title: [Role of prostaglandins in rheumatoid arthritis].

Journal: Nihon rinsho. Japanese journal of clinical medicine20050101

Title: Inhibition of TNF-alpha promoter activity and synthesis by A11-99-1, a new cyclopentenone from the ascomycete Mollisia melaleuca.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences20050101

Title: Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids20050101

Title: Effects of cyclopentenone prostaglandins on the expression of heme oxygenase-1 in MCF-7 cells.

Journal: Annals of the New York Academy of Sciences20041201

Title: Synthesis of 4'-methyl and 4'-cyano carbocyclic 2',3'-didehydro nucleoside analogues via 1,4-addition to substituted cyclopentenones.

Journal: The Journal of organic chemistry20041126

Title: Protein thiol modification by 15-deoxy-Delta12,14-prostaglandin J2 addition in mesangial cells: role in the inhibition of pro-inflammatory genes.

Journal: Molecular pharmacology20041101

Title: Targeting of epidermal growth factor receptor by cyclopentenone prostaglandin 15-Deoxy-Delta12,14-prostaglandin J2 in human oral squamous carcinoma cells.

Journal: Cancer letters20040728

Title: Allenes and transition metals: a diverging approach to heterocycles.

Journal: Organic letters20040624

Title: Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers.

Journal: Bioorganic & medicinal chemistry20040615

Title: 15-deoxy-Delta12,14-prostaglandin J2 inhibits glucocorticoid binding and signaling in macrophages through a peroxisome proliferator-activated receptor gamma-independent process.

Journal: Journal of immunology (Baltimore, Md. : 1950)20040615

Title: Antifungal cyclopentenediones from Piper coruscans.

Journal: Journal of the American Chemical Society20040609

Title: Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects.

Journal: The Journal of organic chemistry20040528

Title: Phosphine catalyzed alpha-arylation of enones and enals using hypervalent bismuth reagents: regiospecific enolate arylation via nucleophilic catalysis.

Journal: Journal of the American Chemical Society20040505

Title: Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using delta-amino beta-ketophosphonates and ring-closing metathesis (RCM).

Journal: Organic letters20040415

Title: The biphasic effects of cyclopentenone prostaglandins, prostaglandin J(2) and 15-deoxy-Delta(12,14)-prostaglandin J(2) on proliferation and apoptosis in rat basophilic leukemia (RBL-2H3) cells.

Journal: Biochemical pharmacology20040401

Title: Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes).

Journal: Phytochemistry20040401

Title: 15d-PGJ2 inhibits oxidized LDL-induced macrophage proliferation by inhibition of GM-CSF production via inactivation of NF-kappaB.

Journal: Biochemical and biophysical research communications20040213

Title: Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-beta-lactams via Baylis-Hillman or bromoallylation reactions.

Journal: The Journal of organic chemistry20040206

Title: New Fischer carbene complexes of rhodium(i): preparation and 2-cyclopentenone ring synthesis by annelation to alkynes.

Journal: Journal of the American Chemical Society20040121

Title: The cyclopentenone product of lipid peroxidation, 15-A2t-isoprostane, is efficiently metabolized by HepG2 cells via conjugation with glutathione.

Journal: Chemical research in toxicology20040101

Title: An endogenous electrophile that modulates the regulatory mechanism of protein turnover: inhibitory effects of 15-deoxy-Delta 12,14-prostaglandin J2 on proteasome.

Journal: Biochemistry20031202

Title: Unexpected sensitivity of synthetic Renilla luciferase control vectors to treatment with a cyclopentenone prostaglandin.

Journal: BioTechniques20031201

Title: Cyclopentenone prostaglandins induce lymphocyte apoptosis by activating the mitochondrial apoptosis pathway independent of external death receptor signaling.

Journal: Journal of immunology (Baltimore, Md. : 1950)20031115

Title: Practical synthesis of D- and l-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus).

Journal: The Journal of organic chemistry20031114

Title: Isomerization-cyclization approach to the synthesis of 2-hydroxy-5-alkylidene-cyclopent-2-enones.

Journal: Organic letters20031030

Title: Urease inhibitory activity of simple alpha,beta-unsaturated ketones.

Journal: Life sciences20031024

Title: 2-Cyclopenten-1-one and prostaglandin J2 reduce restenosis after balloon angioplasty in rats: role of NF-kappaB.

Journal: FEBS letters20031009

Title: Structural requirements of cyclopentenone prostaglandins to induce endothelial cell apoptosis.

Journal: Biochemical and biophysical research communications20030725

Title: The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis.

Journal: Journal of the American Chemical Society20030716

Title: Thioredoxin as a molecular target of cyclopentenone prostaglandins.

Journal: The Journal of biological chemistry20030711

Title: Anti-inflammatory activity of 15-deoxy-delta12,14-PGJ2 and 2-cyclopenten-1-one: role of the heat shock response.

Journal: Molecular pharmacology20030701

Title: Two new cyclopentenone derivatives and a new cyclooctadienone derivative from Erigeron annuus (L.) PERS., Erigeron philadelphicus L., and Erigeron sumatrensis RETZ.

Journal: Chemical & pharmaceutical bulletin20030701

Title: Chemical synthesis and cytotoxicity of dihydroxylated cyclopentenone analogues of neocarzinostatin chromophore.

Journal: Bioorganic & medicinal chemistry letters20030616

Title: Role of heme oxygenase-1 protein in the neuroprotective effects of cyclopentenone prostaglandin derivatives under oxidative stress.

Journal: The European journal of neuroscience20030601

Title: The cyclopentenone-type prostaglandin 15-deoxy-delta 12,14-prostaglandin J2 inhibits CD95 ligand gene expression in T lymphocytes: interference with promoter activation via peroxisome proliferator-activated receptor-gamma-independent mechanisms.

Journal: Journal of immunology (Baltimore, Md. : 1950)20030501

Title: Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones.

Journal: Journal of the American Chemical Society20030423

Title: The first example of Nazarov reactions of vinyl cumulenyl ketones.

Journal: Organic letters20030417

Title: Biosynthesis of 14,15-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D(1) pathway.

Journal: Phytochemistry20030201

Title: Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).

Journal: Bioorganic & medicinal chemistry letters20030106

Title: Practical synthesis of D-cyclopent-2-enone, the key intermediate of carbocyclic nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids20030101

Title: Acyl-lithiation of olefins: formation of cyclopentenones from 1-lithio-butadienes and CO.

Journal: Organic letters20021226

Title: Role of structure and pH in cyclization of allene oxide fatty acids: implications for the reaction mechanism.

Journal: Chemistry and physics of lipids20021201

Title: [Cyclopentenone prostaglandin derivatives as neuroprotective compounds].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme20021201

Title: Photodimerisation of enones in a clay microenvironment.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology20021201

Title: Contribution of covalent protein modification to the antiinflammatory effects of cyclopentenone prostaglandins.

Journal: Annals of the New York Academy of Sciences20021101

Title: Formation of highly reactive A-ring and J-ring isoprostane-like compounds (A4/J4-neuroprostanes) in vivo from docosahexaenoic acid.

Journal: The Journal of biological chemistry20020927

Title: The cyclopentenone product of lipid peroxidation, 15-A(2t)-isoprostane (8-isoprostaglandin A(2)), is efficiently conjugated with glutathione by human and rat glutathione transferase A4-4.

Journal: Chemical research in toxicology20020901

Title: Asymmetric cyclopentannelation: camphor-derived auxiliary.

Journal: Journal of the American Chemical Society20020828

Title: Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues.

Journal: Bioorganic & medicinal chemistry letters20020805

Title: Cyclopentenone prostaglandin receptors.

Journal: Prostaglandins & other lipid mediators20020801

Title: Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones.

Journal: Journal of the American Chemical Society20020731

Title: Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes.

Journal: Organic letters20020725

Title: Cobalt-phosphite-catalyzed asymmetric Pauson-Khand reaction.

Journal: The Journal of organic chemistry20020517

Title: A proinflammatory role for the cyclopentenone prostaglandins at low micromolar concentrations: oxidative stress-induced extracellular signal-regulated kinase activation without NF-kappa B inhibition.

Journal: Journal of immunology (Baltimore, Md. : 1950)20020515

Title: The cyclopentenone prostaglandin 15-deoxy-Delta(12,14)-prostaglandin J(2) attenuates the development of acute and chronic inflammation.

Journal: Molecular pharmacology20020501

Title: Epoxyisoprostane and epoxycyclopentenone phospholipids regulate monocyte chemotactic protein-1 and interleukin-8 synthesis. Formation of these oxidized phospholipids in response to interleukin-1beta.

Journal: The Journal of biological chemistry20020301

Title: A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst.

Journal: Angewandte Chemie (International ed. in English)20020118

Title: Systematic studies on structure and physiological activity of cyclic alpha-keto enamines, a novel class of 'cooling' compounds.

Journal: Journal of agricultural and food chemistry20011101

Title: Highly regio- and stereoselective 1,1-cycloaddition of carbon monoxide with 1,4-dilithio-1,3-dienes. Novel synthetic methods for 3-cyclopenten-1-one derivatives.

Journal: Journal of the American Chemical Society20011024

Title: Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction.

Journal: The Journal of organic chemistry20011005

Title: Antiproliferative prostaglandins and the MRP/GS-X pump role in cancer immunosuppression and insight into new strategies in cancer gene therapy.

Journal: Biochemical pharmacology20011001

Title: Syntheses of D- and L-cyclopentenone derivatives using ring-closing metathesis: versatile intermediates for the synthesis of D- and L-carbocyclic nucleosides.

Journal: The Journal of organic chemistry20010921

Title: Lewis base effects in the Baylis-Hillman reaction of imines with cyclohex-2-en-1-one and cyclopent-2-en-1-one.

Journal: Chemical communications (Cambridge, England)20010921

Title: The first reported anionic oxy retro-ene reaction.

Journal: Organic letters20010920

Title: Determination by enantioselective synthesis of the absolute configuration of CPE, a potential intermediate in coronatine biosynthesis.

Journal: Organic letters20010920

Title: Multifunctionalized alpha,beta-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: a stereospecific rearrangement initiated by base.

Journal: Carbohydrate research20010830

Title: Cyclopentenone prostaglandins of the J series inhibit the ubiquitin isopeptidase activity of the proteasome pathway.

Journal: The Journal of biological chemistry20010810

Title: New bioactive cyclopentenone derivatives as inhibitors of the IL-6 dependent signal transduction.

Journal: The Journal of antibiotics20010801

Title: Regioselective nucleophilic additions to cross-conjugated dienone system bearing beta-fluorine: a versatile approach to highly substituted 2-cyclopentenones.

Journal: Organic letters20010726

Title: Discovery of a new efficient chiral ligand for copper-catalyzed enantioselective Michael additions by high-throughput screening of a parallel library.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20010618

Title: Explaining photodermatosis: cyclopentenone vs. alpha-methylene-gamma-lactone natural products.

Journal: Fitoterapia20010601

Title: Cyclopentenone prostaglandins: new insights on biological activities and cellular targets.

Journal: Medicinal research reviews20010501

Title: Cyclopentenone prostaglandins as potential inducers of intracellular oxidative stress.

Journal: The Journal of biological chemistry20010413

Title: Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins.

Journal: Journal of neurochemistry20010401

Title: Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation.

Journal: Journal of leukocyte biology20010401

Title: Change of the reaction pattern by methodological variations in a multicomponent assembly promoted by Ni complexes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20010401

Title: Density functional studies on the Pauson--Khand reaction.

Journal: Journal of the American Chemical Society20010227

Title: A cyclopentenone prostaglandin activates mesangial MAP kinase independently of PPARgamma.

Journal: Biochemical and biophysical research communications20010216

Title: Parallel synthesis and biocatalytic amplification of a cross-conjugated cyclopentenone library.

Journal: Journal of combinatorial chemistry20010101

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