(1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate

Base Information

• Chemical Name: (1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate
• CAS No.: 188885-85-0
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• DSSTox Substance ID: DTXSID70443945
• Nikkaji Number: J828.364H
• Wikidata: Q82261942
• Mol file: 188885-85-0.mol

Synonyms:188885-85-0;(1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate;ethyl (1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylate;SCHEMBL7733029;DTXSID70443945;WTXWGJHLNCVWJH-NJUXHZRNSA-N;AKOS040804622;(1alpha,5alpha)-2-Oxobicyclo[3.1.0]hexane-6alpha-carboxylic acid ethyl ester

Chemical Property of (1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate

Chemical Property:

• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C2C1C(=O)CC2
• Isomeric SMILES: CCOC(=O)[C@H]1[C@H]2[C@@H]1C(=O)CC2

Technology Process of (1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-carboxylate

There total 14 articles about (1S*,5R*,6S*) Ethyl 2-Oxobicyclo[3.1.0]hexane-6-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: 100.0%

ethyl (1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate (188885-82-7) → (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester (188885-85-0,134176-18-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0957-4166(97)00001-3

Reference yield: 98.0%

2-hydroxy-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester (1246564-20-4) → (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester (188885-85-0,134176-18-4)

Guidance literature:

With chromium trioxide-pyridine complex; In dichloromethane;

DOI:10.1016/j.tetasy.2010.04.051

Reference yield: 80.0%

(+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid (186541-47-9) → (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester (188885-85-0,134176-18-4)

Guidance literature:

With ethanol; sulfuric acid; at 45 ℃; for 1.25h;

upstream raw materials:

ethyl (1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate

(1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

(3aR,3bR,4S,4aS,5aR)-hexahydro-2,2-dimethyl-5-oxocyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4-carboxylic acid ethyl ester

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

Downstream raw materials:

(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

eglumetad

2,2-dimethylpropanoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester