118169-12-3

Basic information

• Product Name: (R)-methyl 2-((diphenylmethylene)amino)pent-4-enoate
• Synonyms: (R)-methyl 2-((diphenylmethylene)amino)pent-4-enoate
• CAS NO: 118169-12-3
• Molecular Weight: 293.365
• Mol File: 118169-12-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (R)-methyl 2-((diphenylmethylene)amino)pent-4-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl 2-((diphenylmethylene)amino)pent-4-enoate(118169-12-3)
• EPA Substance Registry System: (R)-methyl 2-((diphenylmethylene)amino)pent-4-enoate(118169-12-3)

Safety Data

• Hazardous Substances Data: 118169-12-3(Hazardous Substances Data)

Upstream product

• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 106-95-6 allyl bromide 
• 1013-88-3 Benzophenone imine 
• 220280-64-8 (4S,5R)-(-)-1-[2'-(diphenylmethyleneamino)acetyl]-3,4-dimethyl-5-phenyl-2-imidazolidinone 
• 67-56-1 methanol 
• 220280-69-3 (4S,5R)-1-[(S)-2-(Benzhydrylidene-amino)-pent-4-enoyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 591-87-7 Allyl acetate 
• 91-00-9 Benzhydrylamine 
• 173201-94-0 methyl N-(diphenylmethyl)iminoacetate 
• 167904-79-2 methyl (R,S)-2-(N-diphenylmethylidene)aminopent-4-ynoate 
• 4530-20-5 BOC-glycine 
• 4659-45-4 2,6-Dichlorobenzoyl chloride 
• 1469-70-1 allyl ethyl carbonate 

Downstream Products

• 150652-96-3 (R)-2-(tert-butoxycarbonyl)amino-4-pentenoic acid methyl ester 
• 188359-85-5 (R)-tert-butyl (1-hydroxypent-4-en-2-yl)carbamate 
• 115289-55-9 methyl DL-2-amino-4-pentenoate hydrochloride 

Relevant articles and documents

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

Highly enantioselective alkylation of glycine methyl and ethyl ester derivatives under phase-transfer conditions: Its synthetic advantage

Phase-transfer alkylation of the benzophenone Schiff base of glycine methyl or ethyl ester (2) was found to be catalyzed by 3,4,5-F 3-C6H2-NAS-Br [(S,S)-1] with high efficiency and excellent enantioselectivity. This procedure allows facile derivatization of the resulting alkylation products to other synthetically useful chiral building blocks.