56512-51-7

Basic information

• Product Name: vinylglycine
• Synonyms: vinylglycine;(2S)-2-Amino-3-butenoic acid;2-Vinyl-L-glycine
• CAS NO: 56512-51-7
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• Mol File: 56512-51-7.mol

Chemical Properties

• Boiling Point: 256.1°Cat760mmHg
• Flash Point: 108.7°C
• Appearance: /
• Density: 1.144g/cm³
• PKA: 1.99±0.10(Predicted)
• CAS DataBase Reference: vinylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: vinylglycine(56512-51-7)
• EPA Substance Registry System: vinylglycine(56512-51-7)

Safety Data

• Hazardous Substances Data: 56512-51-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Vinylglycine is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its capacity to inhibit methionine biosynthesis makes it a potential agent for controlling methionine-dependent tumors, offering a novel approach to cancer treatment.
Used in Agrochemical Industry:
While vinylglycine's impact on plants is primarily negative due to its toxicity, its use in agrochemicals can be strategic for controlling the growth of certain plants or pests. However, it is crucial to manage its application to prevent detrimental effects on agricultural crops and the environment.
Used in Neurodegenerative Disease Research:
Vinylglycine has been studied for its potential role in the treatment of neurodegenerative diseases. Its mechanism of action, related to methionine metabolism, suggests it may have therapeutic benefits in managing or treating such conditions, although further research is necessary to confirm its efficacy and safety in this context.

Upstream product

• 100038-68-4 2-tert-Butoxycarbonylamino-but-3-enoic acid methyl ester 
• 104523-58-2 2-benzyl 2-N-tert-butoxycarbonylamino-3-butenoate 
• 70562-47-9 ethyl 2-acetamido-2-(ethoxycarbonyl)but-3-enoate 
• 107-93-7 (E)-but-2-enoic acid 
• 600-17-9 vinyl glycolic acid 
• 133559-28-1 2-(Benzhydrylidene-amino)-but-3-enoic acid methyl ester 

Downstream Products

• 617-65-2 Glutamic acid 
• 6667-60-3 2-amino-3-methylbutanedioic acid 
• 59-51-8 DL-methionine 
• 171077-04-6 (+/-)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-butenoic acid 

Relevant articles and documents

Enantioselective synthesis of α-alkenyl α-amino acids via N-H insertion reactions

A new highly enantioselective route to α-alkenyl α-amino acid derivatives, which are important naturally occurring compounds with attractive bioactivity and synthetic utility, was developed using a N-H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids under mild, neutral conditions. This reaction has a broad substrate scope, a fast reaction rate (turnover frequency > 6000 h-1), a high yield (61-99%), and excellent enantioselectivity (83-98% ee). The chiral spiro phosphoric acid, which is proposed to realize the enantioselectivity of the insertion reaction by promoting the proton transfer of a ylide intermediate by acting as a chiral proton shuttle catalyst, can suppress several usual side reactions of vinyldiazoacetates and broaden the applications of these versatile carbene precursors in organic synthesis. To our knowledge, it is the first highly enantioselective carbene insertion reaction of vinyldiazoacetates with heteroatom-hydrogen bonds in which the heteroatom has lone-pair electrons.

Simple Synthesis of L- and D-Vinylglycine (2-Aminobut-3-enoic Acid) and Related Amino Acid

A three-step synthesis of vinylglycine 1 has been developed using a readily available starting material (but-3-enenitrile 2), based on the Neber rearrangement of the corresponding N-chloroimidate, and using cheap, convenient reagents.Also described is a convenient optical resolution of the N-tert-butoxycarbonyl derivative by papain-catalysed enantioselective esterifucation in a two-phase system.From the optically active amino acid, related amino acids obtained via epoxidation, dihydroxylation and cyclopropanation have been prepared.The related β,γ-unsaturated amino acids (E)-2-aminopent-3-enoic acid 20 and (E)-2-amino-3-methylpent-3-enoic acid 22 have been synthesised using the same approach.

Polyenolates of unsaturated carboxylic acids in synthesis. Synthesis of unsaturated α-amino acids and γ-hydrazino acids

Regioselective reaction of lithium diene- and triene-diolates 1 and 2 with o-diphenylphosphinyl hydroxylamine affords unsaturated α-amino acids 3 and 4. Addition to DEAD leads selectively to γ-hydrazino unsaturated acids 5 and 6.

ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE α-CARBON OF α-AMINOACIDS

In this report, we describe three possibilities for aminoacid synthesis using an enantioselective electrophilic process.Thus, enantioselective carboxylation, alkylation and protonation of Schiff bases yield optically active aminoacids with e.e. up to 76percent.

Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines

Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.

Synthesis of Protected Racemic β,γ-Unsaturated-α-Amino Acids via γ-Phenylseleno-α,β-Unsaturated Esters

Oxidative rearrangement of γ-phenylseleno-α,β-unsaturated esters (1) with the N-chlorosuccinimide/N,N-diisopropylethylamine/alkyl carbamate reagent combination affords preparatively useful yields of protected β,γ-unsaturated-α-amino acids (2).