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5807-14-7,MFCD00043003
Catalog No.:AA0038JI

5807-14-7 | 1,3,4,6,7,8-Hexahydro-2h-pyrimido[1,2-a]pyrimidine

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1g
98%
in stock  
$10.00   $7.00
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5g
97%
in stock  
$13.00   $9.00
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10g
95%
in stock  
$18.00   $13.00
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25g
98%
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$42.00   $29.00
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100g
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$134.00   $94.00
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500g
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$669.00   $468.00
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  • Technical Information
  • Properties
  • Literature
  • Application
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0038JI
Chemical Name:
1,3,4,6,7,8-Hexahydro-2h-pyrimido[1,2-a]pyrimidine
CAS Number:
5807-14-7
Molecular Formula:
C7H13N3
Molecular Weight:
139.1982
MDL Number:
MFCD00043003
SMILES:
C1CNC2=NCCCN2C1
Properties
Computed Properties
 
Complexity:
153  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
XLogP3:
-0.3  

Literature

Title: Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles.

Journal: Organic & biomolecular chemistry 20120707

Title: Synthesis, structure and unique reactivity of the ethylzinc derivative of a bicyclic guanidine.

Journal: Dalton transactions (Cambridge, England : 2003) 20120521

Title: One-pot synthesis of trichloromethyl carbinols from primary alcohols.

Journal: The Journal of organic chemistry 20120518

Title: A hydrogen-bridged adduct 3,4,6,7,8,9-hexa-hydro-2H-pyrimido[1,2-a]pyrimidin-1-ium [1,3-bis-(tert-butyl-dimethyl-sil-yloxy)-1,3-bis-(pyridin-2-yl)propan-2-yl-idene]nitro-nate acetonitrile monosolvate.

Journal: Acta crystallographica. Section E, Structure reports online 20110901

Title: X-ray crystallographic, FT-IR, and density functional theory studies of the salt formed between dipicrylamine and 1,5,7-triazabicyclo[4.4.0]dec-1-ene.

Journal: The journal of physical chemistry. A 20110804

Title: Direct aldol reactions catalyzed by a heterogeneous guanidinium salt/proline system under solvent-free conditions.

Journal: Organic letters 20110617

Title: Theoretical mechanistic study of the TBD-catalyzed intramolecular aldol reaction of ketoaldehydes.

Journal: The Journal of organic chemistry 20100716

Title: Catalytic coupling of CO2 with epoxide over supported and unsupported amines.

Journal: The journal of physical chemistry. A 20100325

Title: Coordination of neutral, methylene bridged bis-guanidyls at palladium.

Journal: Dalton transactions (Cambridge, England : 2003) 20100214

Title: A short, unsupported CuI...CuI interaction, 2.65 A, in a dinuclear guanidine chloride complex.

Journal: Chemical communications (Cambridge, England) 20100107

Title: Proof by EPR spectroscopy that the unpaired electron in an Os(2)(7+) species is in a delta* metal-based molecular orbital.

Journal: Inorganic chemistry 20100104

Title: Cyclic guanidine organic catalysts: what is magic about triazabicyclodecene?

Journal: The Journal of organic chemistry 20091218

Title: Superbasicity of a bis-guanidino compound with a flexible linker: a theoretical and experimental study.

Journal: Journal of the American Chemical Society 20091125

Title: Lanthanide metallocene complexes of the 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinato Ligand, (hpp)1-.

Journal: Inorganic chemistry 20081201

Title: A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene.

Journal: Dalton transactions (Cambridge, England : 2003) 20080828

Title: On the performance of ligand field molecular mechanics for model complexes containing the peroxido-bridged [Cu2O2]2+ center.

Journal: Inorganic chemistry 20080407

Title: Structure and vibrational spectrum of the hydrogen-bonded system between 4-tert-butylphenol and N-bases: Ab initio and DFT studies.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080201

Title: A Lewis-basic, dionio-substituted phosphane.

Journal: Chemical communications (Cambridge, England) 20071228

Title: Dinuclear and tetranuclear gold-nitrogen complexes. Solvent influences on oxidation and nuclearity of gold guanidinate derivatives.

Journal: Inorganic chemistry 20071224

Title: Nucleophilic activity of a linked bis{guanidine} leading to formation of a dicationic C4N4-heterocycle.

Journal: Organic & biomolecular chemistry 20071221

Title: The mechanism of TBD-catalyzed ring-opening polymerization of cyclic esters.

Journal: The Journal of organic chemistry 20071207

Title: Theoretical study of the structures and vibrational spectra of the hydrogen-bonded systems of 4-cyanophenol with N-bases.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20071101

Title: Triazabicyclodecene: an effective isotope exchange catalyst in CDCl(3).

Journal: The Journal of organic chemistry 20070622

Title: Stepwise nucleophilic substitution of manganocene, syntheses and structures of the dimer [CpMn(hpp)]2 and the unusual manganate cage [LiMn(hpp)3]2 (hppH = 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2,a]pyrimidine).

Journal: Dalton transactions (Cambridge, England : 2003) 20070428

Title: Encapsulation of hydride by molecular main group metal clusters: manipulating the source and coordination sphere of the interstitial ion.

Journal: Dalton transactions (Cambridge, England : 2003) 20061221

Title: Grid-based molecular modeling for pharmaceutical salt screening: Case example of 3,4,6,7,8,9-hexahydro-2H-pyrimido (1,2-a) pyrimidinium acetate.

Journal: Journal of pharmaceutical sciences 20061101

Title: Organocatalytic living ring-opening polymerization of cyclic carbosiloxanes.

Journal: Organic letters 20061012

Title: Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters.

Journal: Journal of the American Chemical Society 20060412

Title: Facilitating access to the most easily ionized molecule: an improved synthesis of the key intermediate, W2(hpp)4Cl2, and related compounds.

Journal: Inorganic chemistry 20060109

Title: Expeditious access to the most easily ionized closed-shell molecule, W2(hpp)4.

Journal: Journal of the American Chemical Society 20050810

Title: Spontaneous assembly of a nine-vertex lithium framework encapsulating the peroxide dianion.

Journal: Chemical communications (Cambridge, England) 20050707

Title: An example where orbital relaxation is an important contribution to the Fukui function.

Journal: The journal of physical chemistry. A 20050217

Title: Multiple coordination geometries supported by methylene-linked guanidines.

Journal: Inorganic chemistry 20041129

Title: The structural characteristics of organozinc complexes incorporating N,N'-bidentate ligands.

Journal: Dalton transactions (Cambridge, England : 2003) 20041107

Title: M2(hpp)4Cl2 and M2(hpp)4, where M = Mo and W: preparations, structure and bonding, and comparisons with C2, C2H2, and C2Cl2 and the hypothetical molecules M2(hpp)4(H)2.

Journal: Journal of the American Chemical Society 20031224

Title: Structural and catalytic properties of bis(guanidine)copper(I) halides.

Journal: Inorganic chemistry 20030519

Title: The first structurally confirmed paddlewheel compound with an M(2)(7+) core: [Os(2)(hpp)(4)Cl(2)](PF(6)).

Journal: Inorganic chemistry 20030210

Title: Closed-shell molecules that ionize more readily than cesium.

Journal: Science (New York, N.Y.) 20021206

Title: The extraordinary ability of guanidinate derivatives to stabilize higher oxidation numbers in dimetal units by modification of redox potentials: structures of Mo(2)(5+) and Mo(2)(6+) compounds.

Journal: Journal of the American Chemical Society 20020807

Application
1,5,7-Triazabicyclo[4.4.0]dec-5-ene serves as a versatile organocatalyst in various chemical transformations. Firstly, it facilitates the aminolysis of esters, enabling the efficient conversion of ester substrates into amine products. Additionally, it acts as a catalyst for the direct addition of P(O)-H bonds (such as dialkyl phosphites and diphenyl phosphonite) across activated alkenes, leading to the formation of valuable phosphorus-containing compounds. Furthermore, polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PTBD) serves as both a base and a reagent scavenger in the synthesis of aryl ethers from phenols and alkyl or aryl halides, enhancing the efficiency and ease of the reaction process. Overall, 1,5,7-Triazabicyclo[4.4.0]dec-5-ene demonstrates significant utility as a catalyst and reagent in diverse organic transformations, offering opportunities for efficient and selective synthesis of complex molecules.
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Tags:5807-14-7 Molecular Formula|5807-14-7 MDL|5807-14-7 SMILES|5807-14-7 1,3,4,6,7,8-Hexahydro-2h-pyrimido[1,2-a]pyrimidine