(2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate

Base Information

• Chemical Name: (2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate
• CAS No.: 92344-02-0
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17900
• DSSTox Substance ID: DTXSID70449124
• Nikkaji Number: J1.444.152B
• Mol file: 92344-02-0.mol

Synonyms:92344-02-0;(2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate;Methyl (2R)-2-methyl-5-oxocyclopentanecarboxylate;METHYL (2R)-2-METHYL-5-OXOCYCLOPENTANE-1-CARBOXYLATE;Cyclopentanecarboxylic acid, 2-methyl-5-oxo-, methyl ester, (2R)-;(2R)-Methyl2-methyl-5-oxocyclopentanecarboxylate;DTXSID70449124;MFCD11502470;AKOS015998821;CS-0108689;A860106;2-Oxo-5beta-methylcyclopentanecarboxylic acid methyl ester

Chemical Property of (2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate

Chemical Property:

• Boiling Point: 219.0±33.0 °C (760 mmHg)
• PSA: 43.37000
• Density: 1.093±0.06 g/cm3 (20 °C, 760 mmHg)
• LogP: 0.77460
• Storage Temp.: 2-8°C
• 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:

97% ^*data from raw suppliers

(2R)-Methyl2-methyl-5-oxocyclopentanecarboxylate 95+% ^*data from reagent 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)C1C(=O)OC

Technology Process of (2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate

There total 4 articles about (2R)-Methyl 2-methyl-5-oxocyclopentanecarboxylate 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: 97.0%

(5R)-2-isopropylidene-5-methylcyclopentanecarboxylic acid methyl ester (2005-58-5,2847-54-3,7712-69-8,30165-01-6,92076-03-4,141193-83-1) → methyl (2R)-2-methyl-5-oxocyclopentane-1-carboxylate (92344-02-0)

Guidance literature:

(5R)-2-isopropylidene-5-methylcyclopentanecarboxylic acid methyl ester; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.416667h; Inert atmosphere;

With acetic acid; zinc; In methanol; dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02039

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:

α-diazo methyl 3-oxoheptanoate

(5R)-2-isopropylidene-5-methylcyclopentanecarboxylic acid methyl ester

methanol

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

Downstream raw materials:

N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

N-((3R,3aS,7R,8S)-3,9-Dimethyl-6-oxo-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide

C₂₂H₂₉NO₃S