(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

Base Information

• Chemical Name: (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate
• CAS No.: 213316-32-6
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.197
• European Community (EC) Number: 966-309-6
• Nikkaji Number: J1.466.702D
• Mol file: 213316-32-6.mol

Synonyms:(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate;213316-32-6;746657-36-3;ETHYL (1R,2S)-1-AMINO-2-ETHENYLCYCLOPROPANE-1-CARBOXYLATE;Rel-ethyl (1R,2S)-1-amino-2-vinylcyclopropane-1-carboxylate;Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)-rel-;(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester hydrochloride;SCHEMBL374714;NBJXCTLFPNBZSG-HTRCEHHLSA-N;Cyclopropanecarboxylic acid,1-amino-2-ethenyl-,ethyl ester,(1R,2S)-;AKOS006344252;AC-28939;BS-25976;CS-0000379;A852274;(1R,2S)-1-amino-1-ethoxycarbonyl-2-vinylcyclopropane;ethyl (1R,2S)-1-amino-2-vinylcyclopropane-carboxylate;(1R,2S)-1-amino-2-vinyl-cyclopropanecarboxylic acid ethyl ester;Cyclopropanecarboxylic acid,1-amino-2-ethenyl-,ethyl ester,(1R,2S)-(9ci);Cyclopropanecarboxylic acid,1-amino-2-ethenyl-,ethyl ester,(1R,2S)-rel-(9ci)

Chemical Property of (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 0.563mmHg at 25°C
• Boiling Point: 189.675°C at 760 mmHg
• PKA: 6.27±0.40(Predicted)
• Flash Point: 61.357°C
• PSA: 52.32000
• Density: 1.156g/cm³
• LogP: 1.15320
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

(1R,2S)-REL-1-AMINO-2-ETHENYL-CYCLOPROPANECARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC1C=C)N
• Isomeric SMILES: CCOC(=O)[C@]1(C[C@H]1C=C)N

Technology Process of (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

There total 35 articles about (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester (S)-O-3,5-dichlorobenzoyl lactate (1352613-23-0) → (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate (746657-36-3,213316-32-6,259221-73-3)

Guidance literature:

With sodium hydroxide; In water; toluene; at 0 - 10 ℃;

Reference yield: 90.0%

N-Boc-(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester (259217-95-3,213316-49-5) → (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate (746657-36-3,213316-32-6,259221-73-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00418

Reference yield: 85.0%

(E)-1,4-dibromobutene (821-06-7) + ethyl N-benzylideneglycinate (40682-54-0) → (1R,2S)/(1S,2R) 1-amino-2-vinylcyclopropane carboxylic acid ethyl ester (787548-29-2,213316-32-6,259221-73-3)

Guidance literature:

(E)-1,4-dibromobutene; ethyl N-benzylideneglycinate; With ethanol; sodium; In toluene; at 0 ℃; for 2h;

With hydrogenchloride; In water; toluene; at 0 - 30 ℃; Solvent;

upstream raw materials:

(Z)-but-2-ene-1,4-diyl dimethanesulfonate

(E)-1,4-dibromobutene

[(benzylidene)amino]acetic acid ethyl ester

ethyl N-benzylideneglycinate

Downstream raw materials:

(1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate

(1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester

(1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid

(1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester