Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)-

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)-
• CAS No.: 345905-96-6
• Molecular Formula: C12H13ClO2
• Molecular Weight: 224.687
• DSSTox Substance ID: DTXSID30426991
• Nikkaji Number: J457.994A
• Wikidata: Q82239768
• Mol file: 345905-96-6.mol

Synonyms:345905-96-6;Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)-;ethyl (1S,2S)-2-(4-chlorophenyl)cyclopropane-1-carboxylate;DTXSID30426991;AKOS027470083;H11208;2beta-(4-Chlorophenyl)-1alpha-cyclopropanecarboxylic acid ethyl ester

Chemical Property of Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)-

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 224.0604073
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC1C2=CC=C(C=C2)Cl
• Isomeric SMILES: CCOC(=O)[C@H]1C[C@@H]1C2=CC=C(C=C2)Cl

Technology Process of Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)-

There total 7 articles about Cyclopropanecarboxylic acid, 2-(4-chlorophenyl)-, ethyl ester, (1S,2S)- 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: 99.0%

diazoacetic acid ethyl ester (623-73-4) + 4-vinylbenzyl chloride (1073-67-2,24991-47-7) → ethyl trans-2-(4-chlorophenyl)cyclopropane-1-carboxylate (345905-96-6)

Guidance literature:

With sodium dithionite; In aq. phosphate buffer; at 20 ℃; pH=7; stereoselective reaction;

DOI:10.1021/acscatal.7b02583

Reference yield: 50.7%

diazoacetic acid ethyl ester (623-73-4) + 4-vinylbenzyl chloride (1073-67-2,24991-47-7) → ethyl trans-2-(4-chlorophenyl)cyclopropane-1-carboxylate (345905-96-6) + (1R,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylic acid ethyl ester (207279-36-5)

Guidance literature:

With sodium dithionite; c-type cytochrome maquette, C₄₅; In ethanol; at 5 - 25 ℃; for 2h; pH=8.6; stereoselective reaction; Catalytic behavior; Glovebox; Inert atmosphere; Enzymatic reaction;

DOI:10.1073/pnas.1915054117

Reference yield:

diazoacetic acid ethyl ester (623-73-4) + 4-vinylbenzyl chloride (1073-67-2,24991-47-7) → ethyl trans-2-(4-chlorophenyl)cyclopropane-1-carboxylate (345905-96-6) + ethyl (1S,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylate (395683-40-6) + ethyl (1R,2S)-2-(4-chlorophenyl)cyclopropane-1-carboxylate (395683-39-3) + (1R,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylic acid ethyl ester (207279-36-5)

Guidance literature:

With copper(I) triflate; copper(I)-chiral bipyridine complex C₂₂H₃₂ClCuN₂O₂; In chloroform; for 20h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1039/a706754b

upstream raw materials:

diazoacetic acid ethyl ester

4-vinylbenzyl chloride

glycine ethyl ester hydrochloride