2-oxocyclohexanepropionic acid

Base Information

• Chemical Name: 2-oxocyclohexanepropionic acid
• CAS No.: 2275-26-5
• Molecular Formula: C9H14 O3
• Molecular Weight: 170.208
• Hs Code.: 2918300090
• European Community (EC) Number: 218-895-3
• NSC Number: 119501
• DSSTox Substance ID: DTXSID601305776
• Nikkaji Number: J22.853B
• Mol file: 2275-26-5.mol

Synonyms:Cyclohexanepropionicacid, 2-oxo- (6CI,7CI); 2-(2-Carboxyethyl)cyclohexanone;2-Oxocyclohexanepropanoic acid; 3-(2-Oxocyclohexyl)propionic acid; NSC 119501

Chemical Property of 2-oxocyclohexanepropionic acid

Chemical Property:

• Vapor Pressure: 2.02E-05mmHg at 25°C
• Melting Point: 62 °C
• Boiling Point: 337°Cat760mmHg
• PKA: 4.60±0.10(Predicted)
• Flash Point: 171.8°C
• PSA: 54.37000
• Density: 1.122g/cm³
• LogP: 1.61050
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%min ^*data from raw suppliers

3-(2-Oxo-cyclohexyl)-propionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)CCC(=O)O
• Uses: 3-(2-Oxo-cyclohexyl)-propionic Acid is an intermediate in the synthesis of Hexahydrocoumarin (H293905), a derivative of Coumarin (C755380) that is used as a fragrance ingredient.

Technology Process of 2-oxocyclohexanepropionic acid

There total 22 articles about 2-oxocyclohexanepropionic acid 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: 90.0%

3-(2-oxocyclohexyl)propionic acid ethyl ester (4095-02-7) → 3-(2-oxocyclohexyl)propionic acid (2275-26-5)

Guidance literature:

With potassium hydroxide; In water; at 20 ℃; for 4h;

DOI:10.1246/bcsj.75.801

Reference yield: 90.0%

ethyl 2-oxocyclohexane carboxylate (1655-07-8) + ethyl acrylate (140-88-5,9003-32-1) → 3-(2-oxocyclohexyl)propionic acid (2275-26-5)

Guidance literature:

ethyl 2-oxocyclohexane carboxylate; ethyl acrylate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In water; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.7b01963

Reference yield: 63.0%

cyclohexanone-2-propionitrile (4594-78-9) → 3-(2-oxocyclohexyl)propionic acid (2275-26-5)

Guidance literature:

at 30 ℃; for 120h; Rhodococcus sp. (SP 361), pH 7;

DOI:10.1016/S0957-4166(00)80215-3

upstream raw materials:

(2-oxo-cyclohexylmethyl)-malonic acid diethyl ester

3-(1-ethoxycarbonyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

ethyl 3-chloropropanoate

cyclohexanone

Downstream raw materials:

3,4,5,6,7,8-hexahydro-chromen-2-one

3-Oxo-5-(2-oxocyclohexyl)-2-(triphenylphosphoranyliden)pentananilid

3-(2-oxocyclohexyl)propionic acid ethyl ester

Methyl (Z)-2-(phenylselanylcarbonylethyl)cyclohexylideneacetate

Refernces

• 1、 Openshaw,Robinson. "-". . p. 941,945. Retrieved 1937.
• 2、 Yang, Wei,Sun, Xianyu,Yu, Wenbo,Rai, Rachita,Deschamps, Jeffrey R.,Mitchell, Lauren A.,Jiang, Chao,Mackerell, Alexander D.,Xue, Fengtian. "Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids". supporting information. p. 3070 - 3073. Retrieved 2015/06/30.
• 3、 Fogal, Erica,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio. "Synthesis of enantiomerically pure bicyclic condensed δ-lactones via microbial reduction and enzymic resolution strategies". . p. 2599 - 2614. Retrieved 2007/10/03.