Methyl 2-methyl-4-oxocyclohex-2-enecarboxylate

Base Information

• Chemical Name: Methyl 2-methyl-4-oxocyclohex-2-enecarboxylate
• CAS No.: 35490-07-4
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID10452056
• Nikkaji Number: J502.606G
• Mol file: 35490-07-4.mol

Synonyms:35490-07-4;METHYL 2-METHYL-4-OXOCYCLOHEX-2-ENECARBOXYLATE;134209-76-0;methyl 2-methyl-4-oxocyclohex-2-ene-1-carboxylate;2-methyl-4-oxo-1-cyclohex-2-enecarboxylic acid methyl ester;2-Cyclohexene-1-carboxylic acid, 2-methyl-4-oxo-, methyl este;Methyl 2-methyl-4-oxo-cyclohex-2-ene-1-carboxylate;SCHEMBL2015282;DTXSID10452056;AGOJIHXCXNTMPM-UHFFFAOYSA-N;2-Methyl-4-oxo-2-cyclohexene-1-carboxylic acid methyl ester;CS-0459893;A822835;METHYL2-METHYL-4-OXOCYCLOHEX-2-ENECARBOXYLATE;1-Methyl-3-oxocyclohexene-6-carboxylic acid methyl ester

Chemical Property of Methyl 2-methyl-4-oxocyclohex-2-enecarboxylate

Chemical Property:

• Boiling Point: 254.9 °C at 760 mmHg
• Flash Point: 107.6 °C
• PSA: 43.37000
• Density: 1.107 g/cm³
• LogP: 1.08480
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 240

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-methyl-4-oxocyclohex-2-enecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CCC1C(=O)OC

Technology Process of Methyl 2-methyl-4-oxocyclohex-2-enecarboxylate

There total 7 articles about Methyl 2-methyl-4-oxocyclohex-2-enecarboxylate 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: 83.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acetoacetic acid methyl ester (105-45-3) → methyl 2-methyl-4-oxocyclohex-2-enecarboxylate (35490-07-4,134209-76-0)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 0 ℃; for 31h; Reflux;

DOI:10.1021/ja1076102

Reference yield: 28.0%

methyl vinyl ketone (78-94-4,25038-87-3) + acetoacetic acid methyl ester (105-45-3) → methyl 2-methyl-4-oxocyclohex-2-enecarboxylate (35490-07-4,134209-76-0)

Guidance literature:

With sodium methylate; In methanol; for 12h; Heating;

DOI:10.1246/cl.2000.888

Reference yield:

acetoacetic acid methyl ester (105-45-3) → methyl 2-methyl-4-oxocyclohex-2-enecarboxylate (35490-07-4,134209-76-0)

Guidance literature:

With piperidine; formaldehyd; Erwaermen des Reaktionsprodukts mit aethanol. Natriumaethylat und anschliessendes Behandeln mit wss. Schwefelsaeure;

DOI:10.1021/ja01264a515

upstream raw materials:

acetoacetic acid methyl ester

2-acetyl-5-oxo-hexanoic acid methyl ester

diethyl 2-oxo-3-butenylphosphonate

4-methyl-6-oxo-cyclohex-4-ene-1,3-dicarboxylic acid dimethyl ester

Downstream raw materials:

4-hydroxy-2-methylbenzoic acid methyl ester

ethyl 2,2-dimethyl-4-oxocyclohexane-1-carboxylate

Refernces

• 1、 Liang, Yu-Feng,Song, Song,Ai, Lingsheng,Li, Xinwei,Jiao, Ning. "A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones". supporting information. p. 6462 - 6467. Retrieved 2018/06/08.
• 2、 -. "THIAZOLE-SUBSTITUTED AMINOHETEROARYLS AS SPLEEN TYROSINE KINASE INHIBITORS". . . Retrieved 2015/07/07.