2-Ethenyl-2-methylcyclohexanone

Base Information

• Chemical Name: 2-Ethenyl-2-methylcyclohexanone
• CAS No.: 63196-62-3
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• UNII: 1WJ1D8JPT3
• Nikkaji Number: J1.113.063A
• Mol file: 63196-62-3.mol

Synonyms:2-Ethenyl-2-methylcyclohexanone;1WJ1D8JPT3;Cyclohexanone, ethenylmethyl-;UNII-1WJ1D8JPT3;63196-62-3;2-Methyl-2-vinylcyclohexanone;SCHEMBL10598024

Chemical Property of 2-Ethenyl-2-methylcyclohexanone

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCCCC1=O)C=C

Technology Process of 2-Ethenyl-2-methylcyclohexanone

There total 8 articles about 2-Ethenyl-2-methylcyclohexanone 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: 82.0%

2-<1-hydroxy-2-(phenylseleno)ethyl>-2-methylcyclohexanone (80533-29-5) → (+/-)-2-Methyl-2-vinylcyclohexan-1-one (63196-62-3)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; for 0.166667h;

DOI:10.1021/jo00348a005

Reference yield: 80.0%

dicarbonyl(cyclopentadienyl)(ethyl vinyl ether)iron tetrafluoroborate + 2-methylcyclohexanone lithium enolate (13670-84-3) → (+/-)-2-Methyl-2-vinylcyclohexan-1-one (63196-62-3)

Guidance literature:

dicarbonyl(cyclopentadienyl)(ethyl vinyl ether)iron tetrafluoroborate; 2-methylcyclohexanone lithium enolate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

In acetonitrile; for 2h; regiospecific reaction; Reflux; Inert atmosphere;

DOI:10.15227/orgsyn.066.0095

Reference yield:

Methanesulfonic acid (1S,6S)-1-methoxy-6-methyl-bicyclo[4.1.0]hept-7-ylmethyl ester → (+/-)-2-Methyl-2-vinylcyclohexan-1-one (63196-62-3)

Guidance literature:

With perchloric acid; In diethyl ether; for 0.5h; Yield given; from 0 deg C to r.t.;

DOI:10.1016/S0040-4039(00)61478-8

upstream raw materials:

2-ethenylcyclohexanone

methyl iodide

2-<1-hydroxy-2-(phenylseleno)ethyl>-2-methylcyclohexanone

1-trimethylsilyloxy-2-methyl-1-cyclohexene

Downstream raw materials:

[1R*(6R*/S*)]-[3,3-Dimethyl-1-(6-methyl-6-vinylcyclohex-1-en-1-yl)hex-5-en-1-oxy]triethylsilane

[1R*(6R*/S*)]-[2,2-Dimethyl-1-(6-methyl-6-vinylcyclohex-1-en-1-yl)pent-4-en-1-oxy]triethylsilane

[1R*(6R*/S*)]-3,3-Dimethyl-1-(6-methyl-6-vinylcyclohex-1-en-1-yl)hex-5-en-1-ol

[1R*(6R*/S*)]-2,2-Dimethyl-1-(6-methyl-6-vinylcyclohex-1-en-1-yl)pent-4-en-1-ol

Refernces

• 1、 Mehta, Goverdhan,Acharyulu, Palle V. R.. "A New Strategy for the α-Vinylation of Ketones : Application to an Enantioselective Synthesis of Sesquiterpene (+)-α-Elemene". . p. 601 - 612. Retrieved 2007/10/03.
• 2、 Chang, Tony C. T.,Rosenblum, Myron,Simms, Nancy. "Vinylation of enolates with a vinyl cation equivalent: trans-3-Methyl-2-vinylcyclohexanone". . p. 95 - 95. Retrieved 2017/05/17.