Methyl 4-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 4-oxocyclohexanecarboxylate
• CAS No.: 6297-22-9
• Molecular Formula: C8H12O3
• Molecular Weight: 156.181
• Hs Code.: 2918300090
• European Community (EC) Number: 613-123-5
• NSC Number: 17321
• DSSTox Substance ID: DTXSID50280517
• Nikkaji Number: J22.828A
• Wikidata: Q72492427
• Mol file: 6297-22-9.mol

Synonyms:methyl 4-oxocyclohexanecarboxylate;6297-22-9;methyl 4-oxocyclohexane-1-carboxylate;4-Oxo-cyclohexanecarboxylic acid methyl ester;METHYL 4-KETOCYCLOHEXANECARBOXYLATE;cyclohexanecarboxylic acid, 4-oxo-, methyl ester;Methyl cyclohexanone-4-carboxylate;methyl4-oxocyclohexanecarboxylate;MFCD00270324;4-oxo-cyclohexane-1-carboxylic acid methyl ester;4-Cyclohexane carboxylic acid methyl ester;4-(Methoxycarbonyl)cyclohexanone;NSC 17321;cyclohexanone-4-carboxylic acid methyl ester;SCHEMBL791232;4-carbomethoxy-1-cyclohexanone;DTXSID50280517;methyl 4-oxocyclohexane carboxylate;methyl 4-oxocyclohexane-carboxylate;methyl 4-ketocyclohexane carboxylate;NSC17321;NSC-17321;AKOS006272504;CS-W005848;PB43190;AS-18457;SY022071;4-keto-cyclohexyl formic acid methyl ester;4-oxocyclohexane carboxylic acid methylester;4-Oxocyclohexanecarboxylic acid methyl ester;AM20070503;FT-0671884;EN300-85391;J-522365

Chemical Property of Methyl 4-oxocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.0646mmHg at 25°C
• Refractive Index: 1.463
• Boiling Point: 230.8 °C at 760 mmHg
• Flash Point: 94.8 °C
• PSA: 43.37000
• Density: 1.111 g/cm³
• LogP: 0.91870
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 164

Purity/Quality:

99%min ^*data from raw suppliers

Methyl4-Oxocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(=O)CC1
• Uses: Methyl 4-Oxocyclohexanecarboxylate is an intermediate for preparation of imidazobenzazepine derivatives as dual H1/5-HT2A antagonists for treatment of sleep disorders.

Technology Process of Methyl 4-oxocyclohexanecarboxylate

There total 22 articles about Methyl 4-oxocyclohexanecarboxylate 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: 97.5%

methyl 4-hydroxycyclohexanecarboxylate (3618-03-9,6125-57-1,17449-76-2) → 4-carbomethoxycyclohexanone (6297-22-9)

Guidance literature:

With Celite; sodium acetate; pyridinium chlorochromate; In acetonitrile; for 3.5h; Ambient temperature;

DOI:10.1021/jo00005a019

Reference yield: 64.0%

trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate (80269-67-6) → 4-carbomethoxycyclohexanone (6297-22-9)

Guidance literature:

With sodium chloride; In water; N,N-dimethyl-formamide; for 48h; Heating;

DOI:10.1055/s-1981-29617

Reference yield: 50.0%

methyl 4-oxobicyclo<3.1.0>hexane-1-carboxylate (154184-56-2) → 4-carbomethoxycyclohexanone (6297-22-9)

Guidance literature:

With lithium perchlorate; triethylamine; In acetonitrile; for 3h; Irradiation;

DOI:10.1016/S0040-4039(00)61464-8

upstream raw materials:

methyl 4-trimethylsilyloxy-3-cyclohexenylcarboxylate

methyl 4-hydroxylbenzoate

methyl 4-hydroxycyclohexanecarboxylate

trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate

Downstream raw materials:

methyl 4-morpholinocyclohex-3-enecarboxylic acid

(1S,3R)-3-Allyl-4-oxo-cyclohexanecarboxylic acid methyl ester

(1S,3S)-3-Allyl-4-oxo-cyclohexanecarboxylic acid methyl ester

4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid ester

Refernces

• 1、 -. "BICYCLIC HETEROARYL DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME". Page/Page column 22-23. . Retrieved 2013/11/05.
• 2、 Lamarche, Matthew J.,Leeds, Jennifer A.,Amaral, Adam,Brewer, Jason T.,Bushell, Simon M.,Deng, Gejing,Dewhurst, Janetta M.,Ding, Jian,Dzink-Fox, Joanne,Gamber, Gabriel,Jain, Akash,Lee, Kwangho,Lee, Lac,Lister, Troy,McKenney, David,Mullin, Steve,Osborne, Colin,Palestrant, Deborah,Patane, Michael A.,Rann, Elin M.,Sachdeva, Meena,Shao, Jian,Tiamfook, Stacey,Trzasko, Anna,Whitehead, Lewis,Yifru, Aregahegn,Yu, Donghui,Yan, Wanlin,Zhu, Qingming. "Discovery of LFF571: An investigational agent for Clostridium difficile infection". supporting information; experimental part. p. 2376 - 2387. Retrieved 2012/06/01.