Methyl 2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 2-oxocyclohexanecarboxylate
• CAS No.: 41302-34-5
• Deprecated CAS: 103533-31-9
• Molecular Formula: C8H12O3
• Molecular Weight: 156.181
• Hs Code.: 29183000
• European Community (EC) Number: 255-306-9
• DSSTox Substance ID: DTXSID20884687
• Nikkaji Number: J320.046I
• Mol file: 41302-34-5.mol

Synonyms:Methyl 2-oxocyclohexanecarboxylate;41302-34-5;2-Methoxycarbonylcyclohexanone;methyl 2-oxocyclohexane-1-carboxylate;2-Carbomethoxycyclohexanone;Cyclohexanecarboxylic acid, 2-oxo-, methyl ester;Methyl cyclohexanone-2-carboxylate;Methyl 2-Oxo-1-cyclohexanecarboxylate;2-Oxocyclohexanecarboxylic acid, methyl ester;EINECS 255-306-9;2-OXO-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER;SCHEMBL3171;ghl.PD_Mitscher_leg0.110;2-methoxylcarbonyl cyclohexanone;Methyl2-oxocyclohexanecarboxylate;DTXSID20884687;methyl-2-oxocyclohexanecarboxylate;methyl 2-oxocyclohexane carboxylate;Methyl 2-oxocyclohexanecarboxylate #;MFCD00077699;AKOS000278431;AKOS016843258;SC11829;DS-15245;CS-0054169;FT-0656468;EN300-68543;F11965;2-oxo-cyclohexane-1-carboxylic acid methyl ester;A825509;Methyl 2-oxocyclohexanecarboxylate, technical, >=90% (GC);2-METHOXYCARBONYLCYCLOHEXANONE;CYCLOHEXANECARBOXYLIC ACID, 2-OXO-, METHYL ESTER;METHYL 2-OXOCYCLOHEXANE-1-CARBOXYLATE;METHYL 2-OXOCYCLOHEXANECARBOXYLATE;METHYL CYCLOHEXANONE-2-CARBOXYLATE

Chemical Property of Methyl 2-oxocyclohexanecarboxylate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.0646mmHg at 25°C
• Refractive Index: n20/D 1.483
• Boiling Point: 230.8 °C at 760 mmHg
• PKA: 12.04±0.20(Predicted)
• Flash Point: 94.8 °C
• PSA: 43.37000
• Density: 1.111 g/cm³
• LogP: 0.91870
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-oxocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1CCCCC1=O
• Uses: Methyl 2-Oxocyclohexanecarboxylate is a novel intermediate for the preparation of TRPA1 antagonists for treatment of pain and other TRPA1-associated diseases. Methyl 2-oxocyclohexanecarboxylate has been used in the synthesis of substituted tetrahydrobenzofuran derivatives via reaction with propargylic esters in the presence of palladium catalyst.

Technology Process of Methyl 2-oxocyclohexanecarboxylate

There total 26 articles about Methyl 2-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: 99.0%

methyl 3-oxohept-6-enoate (30414-57-4) → 2-(methoxycarbonyl)cyclohexanone (41302-34-5)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); ytterbium(III) triflate; In 1,4-dioxane; at 20 ℃; for 10h;

DOI:10.1021/ol0349110

Reference yield: 99.0%

dimethyl 1,7-heptanedioate (1732-08-7) → 2-(methoxycarbonyl)cyclohexanone (41302-34-5)

Guidance literature:

With hydrogenchloride; copper(ll) bromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -78 deg C, 30 min; -78 deg C, 15 min, 2.) RT;

DOI:10.1021/jo00155a047

Reference yield: 98.0%

carbon dioxide (124-38-9,18923-20-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl iodide (74-88-4) → 2-(methoxycarbonyl)cyclohexanone (41302-34-5)

Guidance literature:

With poly(dimethylsiloxane-co-methylhydrosiloxane)trimethylsilyl terminated supported 1-carboxy-6-ethyl-1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 25 - 27 ℃; for 4h; under 760.051 Torr;

DOI:10.1039/c0gc00704h

upstream raw materials:

Dimethyl oxalate

cyclohexanone

acetoacetic acid methyl ester

1,3-dibromo-propane

Downstream raw materials:

3-(1-methoxycarbonyl-2-oxo-cyclohexyl)-propionic acid methyl ester

4,5,6,7-tetrahydro-1H-indazol-3(2H)-one

10-carbomethoxy-Δ^1,9-octal-2-one

methyl 2-oxo-1-(3-oxobutyl)cyclohexane-1-carboxylate

Refernces

• 1、 Li, Jin-Heng,Zhu, Qi-Ming,Liang, Yun,Yang, Dan. "Efficient and reusable PdCl2(MeCN)2/CuCl 2/PEG-400 system for cyclization of alkenyl β-keto esters and amides". . p. 5347 - 5349. Retrieved 2005.
• 2、 Williamson et al.. "-". . p. 3934. Retrieved 1967.
• 3、 -. "Novel BCL-2/BCL-XL inhibitor, pharmaceutical composition and application". Paragraph 0045-0048; 0050-0051. . Retrieved 2020/11/12.
• 4、 Rao, M.V. Krishna,Reddy, K. Nagarjuna,Sridhar,Reddy, B.V. Subba. "Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides". supporting information. . Retrieved 2019/09/16.