Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate

Base Information

• Chemical Name: Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate
• CAS No.: 13949-95-6
• Molecular Formula: C8H12O3
• Molecular Weight: 156.181
• DSSTox Substance ID: DTXSID10501710
• Nikkaji Number: J1.396.753I
• Wikidata: Q82354241
• Mol file: 13949-95-6.mol

Synonyms:Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate;13949-95-6;SCHEMBL15042235;DTXSID10501710

Chemical Property of Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate

Chemical Property:

• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC1C(=O)C
• Isomeric SMILES: CCOC(=O)[C@@H]1C[C@H]1C(=O)C

Technology Process of Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate

There total 10 articles about Ethyl (1R,2R)-2-acetylcyclopropane-1-carboxylate 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%

methyl vinyl ketone (78-94-4,25038-87-3) + ethyl pentamethylene-λ4-sulfanylideneacetate (318990-47-5) → ethyl (1RS,2RS)-2-Acetylcyclopropanecarboxylate (13949-95-6,212137-01-4)

Guidance literature:

In 1,2-dichloro-ethane; at 20 ℃; for 0.5h;

DOI:10.1039/b004367m

Reference yield: 64.0%

diazoacetic acid ethyl ester (623-73-4) + methyl vinyl ketone (78-94-4,25038-87-3) → ethyl (1RS,2RS)-2-Acetylcyclopropanecarboxylate (13949-95-6,212137-01-4)

Guidance literature:

With sulfure de pentamethylene; copper acetylacetonate; In 1,2-dichloro-ethane; at 65 ℃; for 1h;

DOI:10.1039/b004367m

Reference yield:

diethyl trans-cyclopropane-1,2-dicarboxylate (3999-55-1) → ethyl (1RS,2RS)-2-Acetylcyclopropanecarboxylate (13949-95-6,212137-01-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 5 N aq. NaOH / ethanol / 6 h

2: SOCl₂ / Ambient temperature

3: 1.) CuI / 1.) THF, ether, -78 deg C, 30 min, 2.) THF, ether, -78 deg C, 1 h

With sodium hydroxide; copper(l) iodide; thionyl chloride; In ethanol;

DOI:10.1021/jm970497w

upstream raw materials:

methyl vinyl ketone

ethyl (dimethylsulfuranylidene)acetate

(3-Oxo-1-butenyl)triphenylphosphonium-bromid

methyllithium

Downstream raw materials:

3-((1S,2S)-2-Isopropenyl-cyclopropyl)-3-oxo-propionic acid methyl ester

(1R,2R)-2-Acetyl-cyclopropanecarboxylic acid