80003-54-9

Basic information

• Product Name: 1-Amino-2-ethenylcyclopropanecarboxylicacid
• Synonyms: 1-Amino-2-ethenylcyclopropanecarboxylicacid;Cyclopropanecarboxylic acid, 1-amino-2-ethenyl- (9CI);1-Amino-2-vinylcyclopropanecarboxylic acid;1-amino-2-ethenylcyclopropane-1-carboxylic acid
• CAS NO: 80003-54-9
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14116
• Product Categories: AMINOACID
• Mol File: 80003-54-9.mol

Chemical Properties

• Boiling Point: 234.887 °C at 760 mmHg
• Flash Point: 95.856 °C
• Appearance: /
• Density: 1.377 g/cm³
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 1-Amino-2-ethenylcyclopropanecarboxylicacid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-2-ethenylcyclopropanecarboxylicacid(80003-54-9)
• EPA Substance Registry System: 1-Amino-2-ethenylcyclopropanecarboxylicacid(80003-54-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 80003-54-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
1-Amino-2-ethenylcyclopropanecarboxylic acid is used as a research compound for its unique structure and potential applications in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
1-Amino-2-ethenylcyclopropanecarboxylic acid is used as a building block in the development of new pharmaceutical compounds, particularly those that may benefit from its unique structural features, such as the ethenyl and cyclopropane groups.

InChI:InChI=1/C6H9NO2/c1-2-4-3-6(4,7)5(8)9/h2,4H,1,3,7H2,(H,8,9)

Upstream product

• 681260-04-8 (1R,2S)-1-amino-2-vinyl-cyclopropyl carboxylic acid methyl ester 
• 862273-27-6 (1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt 
• 159622-10-3 (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid 
• 213316-32-6 rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 

Downstream Products

• 159622-09-0 (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 159622-10-3 (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid 

Relevant articles and documents

Preparation method for alpha-amino acid

The invention provides a preparation method for an alpha-amino acid and belongs to the pharmaceutical technical field. The preparation method comprises the following steps: in the presence of an alkali, performing a reaction of a metal complex in an organic solvent to obtain a complex; and then hydrolyzing the complex and/or reacting with a protecting agent to obtain the alpha-amino acid or derivatives thereof. The method provided by the invention can simply obtain the amino acid or derivatives thereof without splitting the product, so that the yield is high, the cost is low, and industrial production is facilitated.

Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2-SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex

This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (SN2), homogeneous SN2′ cyclization followed by disassembly of the resultant Ni(ii) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(ii) complex. This journal is

1-AMINO-2-VINYL CYCLOPROPANE CARBOXYLIC ACID AMIDE, SALT OF SAME, AND METHOD FOR PRODUCING SAME

The present invention relates to 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof. By obtaining optically active 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof by hydrolyzing optically active 1-amino-2-vinylcyclopropane carbonitrile or a salt thereof according to the production method of the present invention, 1-amino-2-vinylcyclopropane carboxylic acid amide or a salt thereof, which is useful as a pharmaceutical/agrochemical intermediate, can be easily obtained. The present invention is capable of providing a substrate to be subjected to optical resolution, which enables the production of optically active 1-amino-2-vinylcyclopropane carboxylic acid, which is widely used as a raw material for pharmaceutical and agrochemical products and is especially important as an intermediate for therapeutic agents for hepatitis C, inexpensively with high purity and high yield.

Dynamic kinetic resolution of dehydrocoronamic acid

Dehydrocoronamic acid can be racemised by dehydration of an N-acyl derivative to an azlactone, which undergoes facile racemisation. For the N-trifluoroacetyl derivative, the racemisation process was combined with an enzymatic resolution, to achieve a dynamic kinetic resolution process by which the racemate can be converted to either enantiomer. This journal is the Partner Organisations 2014.

PROCESS FOR PRODUCING SOLID AMINO ACID

The problem to be solved by the present invention is to ea lily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals. The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.