(1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester
• CAS No.: 80796-76-5
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.181
• DSSTox Substance ID: DTXSID00452909
• Nikkaji Number: J631.453H
• Mol file: 80796-76-5.mol

Synonyms:CTK2I7266;80796-76-5;DTXSID00452909;(1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester

Chemical Property of (1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=O)C1C(=O)OC
• Isomeric SMILES: C[C@@H]1CCC(=O)[C@H]1C(=O)OC

Technology Process of (1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester

There total 2 articles about (1S,5R)-2-Oxo-5-methylcyclopentanecarboxylic acid methyl ester 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:

4-methyl-cyclohexane-1,3-dione (14203-46-4) → (1S,2R)-2-Methyl-5-oxo-cyclopentanecarboxylic acid methyl ester (18067-33-9,80796-76-5,92344-02-0,125515-77-7,131235-63-7,132202-11-0,132295-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tosyl azide, triethylamine / CH₂Cl₂ / 2 h / 0 °C

2: N(Et)3 / acetonitrile / 3 h / Irradiation

With 4-toluenesulfonyl azide; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)99336-5

Reference yield:

methanol (67-56-1) + 2-Diazo-4-methylcyclohexane-1,3-dione (122571-21-5) → 3-methyl-2-oxo-cyclopentanecarboxylic acid methyl ester (57964-61-1) + (1S,2R)-2-Methyl-5-oxo-cyclopentanecarboxylic acid methyl ester (18067-33-9,80796-76-5,92344-02-0,125515-77-7,131235-63-7,132202-11-0,132295-15-9)

Guidance literature:

With triethylamine; In acetonitrile; for 3h; Yield given. Yields of byproduct given; Irradiation;

DOI:10.1016/S0040-4039(00)99336-5

upstream raw materials:

methanol

2-Diazo-4-methylcyclohexane-1,3-dione

4-methyl-cyclohexane-1,3-dione

Refernces