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924-44-7,MFCD00044009
Catalog No.:AA0034TG

924-44-7 | Ethyl glyoxalate, 50% in toluene

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0034TG
Chemical Name:
Ethyl glyoxalate, 50% in toluene
CAS Number:
924-44-7
Molecular Formula:
C4H6O3
Molecular Weight:
102.0886
MDL Number:
MFCD00044009
SMILES:
CCOC(=O)C=O
NSC Number:
49206
Properties
Properties
 
BP:
110°C  
Form:
Liquid  
Refractive Index:
1.475  
Stability:
Air Sensitive  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
77  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
7  
Hydrogen Bond Acceptor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
0.4  

Literature

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Journal: Molecular diversity 20120801

Title: Base-catalyzed direct conversion of dipyrromethanes to 1,9-dicarbinols: a [2 + 2] approach for porphyrins.

Journal: Organic letters 20120406

Title: 3-aminopiperidine-based peptide analogues as the first selective noncovalent inhibitors of the bacterial cysteine protease IdeS.

Journal: Journal of medicinal chemistry 20120322

Title: Copper-catalyzed [5+1] annulation of 2-ethynylanilines with an N,O-acetal leading to construction of quinoline derivatives.

Journal: Organic letters 20120203

Title: Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis.

Journal: Journal of the American Chemical Society 20111019

Title: A three-component reaction forming naphthyridones--synthesis of lophocladine analogs.

Journal: Organic letters 20111007

Title: A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles.

Journal: Chemical communications (Cambridge, England) 20110621

Title: Enantioselective organocatalytic Michael-Wittig-Michael-Michael reaction: dichotomous construction of pentasubstituted cyclopentanecarbaldehydes and pentasubstituted cyclohexanecarbaldehydes.

Journal: Organic letters 20110318

Title: 4-(Piperidin-1-yl)-4H-benzo[b]tetra-zolo[1,5-d][1,4]diazepin-5(6H)-one.

Journal: Acta crystallographica. Section E, Structure reports online 20110101

Title: Kinetics and products of gas-phase reactions of ozone with methyl methacrylate, methyl acrylate, and ethyl acrylate.

Journal: The journal of physical chemistry. A 20100819

Title: Polymeric ethyl glyoxylate in an asymmetric aldol reaction catalyzed by diarylprolinol.

Journal: Organic letters 20100702

Title: A straightforward three-component synthesis of alpha-amino esters containing a phenylalanine or a phenylglycine scaffold.

Journal: The Journal of organic chemistry 20100416

Title: Lewis Acid catalyzed three-component hetero-Diels-alder (povarov) reaction of N-arylimines with strained norbornene-derived dienophiles.

Journal: The Journal of organic chemistry 20100205

Title: Catalytic asymmetric three-component Mannich-type reaction of alkenyl trichloroacetates.

Journal: Organic letters 20091119

Title: Synthesis of (S)- and (R)-5-oxo-piperazine-2-carboxylic acid and its application to peptidomimetics.

Journal: The Journal of organic chemistry 20091106

Title: Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles.

Journal: The Journal of organic chemistry 20090904

Title: Asymmetric petasis reactions catalyzed by chiral biphenols.

Journal: Journal of the American Chemical Society 20080604

Title: Organocatalytic synthesis of beta-alkylaspartates via beta-lactone ring opening.

Journal: The Journal of organic chemistry 20071012

Title: Enol esters: versatile substrates for Mannich-type multicomponent reactions.

Journal: Organic letters 20071011

Title: Highly enantioselective carbonyl-ene reactions catalyzed by a hindered silyl-salen-cobalt complex.

Journal: Organic letters 20070927

Title: Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: asymmetric synthesis of beta,gamma-unsaturated alpha-hydroxy esters.

Journal: Organic letters 20070913

Title: The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.

Journal: Beilstein journal of organic chemistry 20070101

Title: A rapid divergent synthesis of highly substituted delta-lactones.

Journal: Organic letters 20061012

Title: Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20060901

Title: Alpha-hydroxy esters via enantioselective hydrogen-mediated C-C coupling: regiocontrolled reactions of silyl-substituted 1,3-diynes.

Journal: Organic letters 20060817

Title: 2-Methyl-(1Z,3E)-butadiene-1,3,4-tricarboxylic acid, 'isoprenetricarboxylic acid'.

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Title: Domino coupling relay approach to polycyclic pyrrole-2-carboxylates.

Journal: Journal of the American Chemical Society 20050810

Title: Self-supported heterogeneous titanium catalysts for enantioselective carbonyl-ene and sulfoxidation reactions.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20050704

Title: Diastereoselective reductive imino-aldol reaction of alpha-imino esters promoted by titanium tetraiodide: synthesis of alpha,beta-diamino esters.

Journal: Organic & biomolecular chemistry 20050621

Title: Synthetic studies toward ecteinascidin 743.

Journal: The Journal of organic chemistry 20050527

Title: Synthesis of the C11-C29 fragment of amphidinolide F.

Journal: Organic letters 20041014

Title: New taxane derivatives: synthesis of baccatin[14,1-d]furan-2-one nucleus and its condensation with the norstatine side chain.

Journal: The Journal of organic chemistry 20041001

Title: Highly diastereo- and enantioselective reactions of enecarbamates with ethyl glyoxylate to give optically active syn and anti alpha-alkyl-beta-hydroxy imines and ketones.

Journal: Angewandte Chemie (International ed. in English) 20040621

Title: The Direct catalytic asymmetric cross-Mannich reaction: a highly enantioselective route to 3-amino alcohols and alpha-amino acid derivatives.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20040419

Title: Highly enantioselective Friedel-Crafts reaction of aromatic amines with ethyl glyoxylate catalyzed by chiral titanium(IV) complexes: practical synthesis of aminomandelic acid derivatives.

Journal: The Journal of organic chemistry 20040109

Title: Solid-phase synthesis of 1-substituted tetrahydroisoquinoline derivatives employing BOC-protected tetrahydroisoquinoline carboxylic acids.

Journal: Journal of combinatorial chemistry 20040101

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Journal: Organic letters 20030724

Title: A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis.

Journal: The Journal of organic chemistry 20030221

Title: C(2)-symmetric Sc(III)-complexes as chiral Lewis acids. Catalytic enantioselective aldol additions to glyoxylate esters.

Journal: Organic letters 20021003

Title: On the intermediates in chiral bis(oxazoline)copper(II)-catalyzed enantioselective reactions--experimental and theoretical investigations.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020415

Title: Cycloaddition reaction of 2-azadienes derived from beta-amino acids with electron-rich and electron-deficient alkenes and carbonyl compounds. Synthesis of pyridine and 1,3-oxazine derivatives.

Journal: The Journal of organic chemistry 20020405

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