Methyl 4-methyl-2-oxocyclopentanecarboxylate

Base Information

• Chemical Name: Methyl 4-methyl-2-oxocyclopentanecarboxylate
• CAS No.: 4463-75-6
• Molecular Formula: C8H12O3
• Molecular Weight: 156.181
• Hs Code.: 2918300090
• European Community (EC) Number: 873-893-5
• DSSTox Substance ID: DTXSID20561461
• Mol file: 4463-75-6.mol

Synonyms:Methyl 4-methyl-2-oxocyclopentanecarboxylate;4463-75-6;methyl 4-methyl-2-oxocyclopentane-1-carboxylate;Methyl 4-Methyl-2-oxo-cyclopentanecarboxylic acid methyl ester;SCHEMBL856267;DTXSID20561461;PMNNPLSKWIHMAT-UHFFFAOYSA-N;MFCD07776758;AKOS006287092;Methyl 4-methyl-2-oxocyclopentane carboxylate;EN300-115337;4-methyl-2-oxo-cyclopentanecarboxylic acid methyl ester

Chemical Property of Methyl 4-methyl-2-oxocyclopentanecarboxylate

Chemical Property:

• Vapor Pressure: 0.122mmHg at 25°C
• Boiling Point: 219oC at 760 mmHg
• Flash Point: 88.1oC
• PSA: 43.37000
• Density: 1.093g/cm3
• LogP: 0.77460
• 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:

98% ^*data from raw suppliers

Methyl4-methyl-2-oxocyclopentanecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(=O)C1)C(=O)OC

Technology Process of Methyl 4-methyl-2-oxocyclopentanecarboxylate

There total 4 articles about Methyl 4-methyl-2-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: 87.0%

dimethyl 3-methylhexanedioate (54576-13-5) → methyl 4-methyl-2-oxocyclopentane-1-carboxylate (4463-75-6)

Guidance literature:

With sodium; In methanol; toluene; for 2.5h; Heating;

Reference yield: 62.0%

methyl 4-methyl-2-oxocyclopent-3-ene-1-carboxylate → methyl 4-methyl-2-oxocyclopentane-1-carboxylate (4463-75-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; Inert atmosphere;

Reference yield:

3-Methyl-2-cyclopenten-1-one (2758-18-1) → methyl 4-methyl-2-oxocyclopentane-1-carboxylate (4463-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.33 h / -78 °C / Inert atmosphere

1.2: 3.33 h / -78 - 20 °C

2.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; lithium diisopropyl amide; In tetrahydrofuran; methanol;

upstream raw materials:

dimethyl 3-methylhexanedioate

3-Methyl-2-cyclopenten-1-one

Downstream raw materials:

4-chloro-6-methyl-2-(methylthio)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

3-methyladipic acid

Refernces

• 1、 Matthews, Randall S.,Oliver, Joel D.,Ward, James F.,Eickhoff, David J.,Strickland, Larry C.. "Total synthesis and X-Ray Crystal Structure of 13,14-Didehydro-11-deoxy-11-methyl-15-oxoprostaglandin E1". . p. 1485 - 1488. Retrieved 2007/10/02.