Cyclohexanepropanoic acid, 2-oxo-, methyl ester

Base Information

• Chemical Name: Cyclohexanepropanoic acid, 2-oxo-, methyl ester
• CAS No.: 10407-33-7
• Deprecated CAS: 58769-44-1
• Molecular Formula: C10H16O3
• Molecular Weight: 184.235
• European Community (EC) Number: 600-517-7
• DSSTox Substance ID: DTXSID70884470
• Nikkaji Number: J23.227K
• Mol file: 10407-33-7.mol

Synonyms:10407-33-7;Cyclohexanepropanoic acid, 2-oxo-, methyl ester;Methyl 3-(2-oxocyclohexyl)propanoate;Methyl 2-oxocyclohexanepropionate;Methyl 3-(2-oxocyclohexyl)propionate;AI3-28143;Methyl 2-oxocyclohexane-3-propionate;SCHEMBL8159406;DTXSID70884470;HMS1578P12;STL450891;AKOS022358660;Methyl 3-(2-oxocyclohexyl)propanoate #;2-(2-methoxycarbonyl-ethyl) cyclohexanone;2-Oxocyclohexanepropionic acid methyl ester;FT-0706531;3-(2-oxo-cyclohexyl)-propionic acid methyl ester

Chemical Property of Cyclohexanepropanoic acid, 2-oxo-, methyl ester

Chemical Property:

• Vapor Pressure: 0.00914mmHg at 25°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCC1CCCCC1=O

Technology Process of Cyclohexanepropanoic acid, 2-oxo-, methyl ester

There total 30 articles about Cyclohexanepropanoic acid, 2-oxo-, 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: 99.0%

1-tri(n-butyl)stannyloxy-1-cyclohexene (17851-97-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3-(2-oxocyclohexyl)propionate (10407-33-7,58769-44-1)

Guidance literature:

With tetrabutylammomium bromide; In tetrahydrofuran; at 25 ℃; for 14h;

DOI:10.1021/jo990062b

Reference yield: 94.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3-(2-oxocyclohexyl)propionate (10407-33-7,58769-44-1)

Guidance literature:

With pyrrolidine; acetic acid; 4-methoxy-phenol; at 130 ℃; for 2h;

DOI:10.1055/s-1997-4462

Reference yield: 89.0%

4-cyclohexen-1-ylmorpholine (670-80-4) + (1-trimethylsiloxy-1-methoxy-allylic)Fe(CO)2NO complex → methyl 3-(2-oxocyclohexyl)propionate (10407-33-7,58769-44-1)

Guidance literature:

In tetrahydrofuran; Stirring of mixt. at room temp. for 15 h.; Extg. (ether), washing of ext. (aq. HCL, H2O), drying (Na2SO4), evapn., chromy. (hexane-ethyl acetate), elem. anal.;

DOI:10.1246/bcsj.64.2965

upstream raw materials:

1-(cyclohex-1-en-1-yl)piperidine

1-(1-Cyclohexen-1-yl)pyrrolidine

4-cyclohexen-1-ylmorpholine

cyclohexanone

Downstream raw materials:

3-(2-Furan-2-yl-2-hydroxy-cyclohexyl)-propionic acid methyl ester

methyl 3-(2-ethylidenecyclohex-1-yl)propionate

methyl 3-<2-hydroxy-2-<1-(trimethylsilyl)-1,2-propadienyl>cyclohexyl>propionate

cyclohexanone

Refernces

• 1、 Matsushita et al.. "-". . p. 3715. Retrieved 1975.
• 2、 Yasuda, Makoto,Shigeyoshi, Yusuke,Shibata, Ikuya,Baba, Akio. "Michael addition of ketone enolates to α,β-unsaturated esters or amides in a one-pot procedure: Highly efficient effect of lithium salt generated in situ on organotin enolate". . p. 233 - 239. Retrieved 2005.
• 3、 Kurahashi, Kei,Takemoto, Yoshiji,Takasu, Kiyosei. "Room-temperature, acid-catalyzed [2+2] cycloadditions: Suppression of side reactions by using a flow microreactor system". . p. 270 - 273. Retrieved 2012.
• 4、 Caldora, Henry P.,Govaerts, Sebastian,Dighe, Shashikant U.,Turner, Oliver J.,Leonori, Daniele. "A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination-Cyclization Approach". supporting information. p. 4272 - 4278. Retrieved 2021/08/13.
• 5、 Kubilius, Rytis,Bagd?inas, Gintautas,Butkus, Eugenijus. "Ring contraction/transannular cyclization of chiral bicyclo[3.3.1] nonanediones mediated by thallium(III) nitrate". scheme or table. p. 346 - 348. Retrieved 2011/02/28.