6,6-Dimethyl-1-Vinylcyclohexene

Base Information

• Chemical Name: 6,6-Dimethyl-1-Vinylcyclohexene
• CAS No.: 18238-29-4
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• DSSTox Substance ID: DTXSID10473968
• Nikkaji Number: J337.820I
• Wikidata: Q82303681
• Mol file: 18238-29-4.mol

Synonyms:6,6-Dimethyl-1-Vinylcyclohexene;18238-29-4;DTXSID10473968;UEWHLMYTUFDQND-UHFFFAOYSA-N;6,6-dimethyl-1-vinyl cyclohexene;6,6-dimethyl-1-vinylcyclohex-1-ene

Chemical Property of 6,6-Dimethyl-1-Vinylcyclohexene

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 161

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC=C1C=C)C

Technology Process of 6,6-Dimethyl-1-Vinylcyclohexene

There total 11 articles about 6,6-Dimethyl-1-Vinylcyclohexene 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: 87.0%

1-ethenyl-2,2-dimethyl-cyclohexanol (18238-28-3) → 6,6-dimethyl-1-vinylcyclohex-1-ene (18238-29-4)

Guidance literature:

With copper(II) sulfate; In benzene; for 2h; Heating;

Reference yield:

2,2-dimethyl-cyclohexanone (1193-47-1) → 6,6-dimethyl-1-vinylcyclohex-1-ene (18238-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / tetrahydrofuran / 2 h / -78 °C

2: 76 percent / potassium bisulfate / 0.17 h / 150 °C

With potassium hydrogensulfate; In tetrahydrofuran;

DOI:10.1021/jo00224a078

Reference yield:

6-iodo-2,2-dimethylhexanenitrile (56475-48-0) → 6,6-dimethyl-1-vinylcyclohex-1-ene (18238-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 - -40 °C / Inert atmosphere

2: tetrahydrofuran / 2 h / Inert atmosphere

3: copper(II) sulfate / benzene / 24 h / 90 °C / Inert atmosphere; Dean-Stark

With tert.-butyl lithium; copper(II) sulfate; In tetrahydrofuran; pentane; benzene;

DOI:10.1021/acs.orglett.6b03682

upstream raw materials:

1-ethenyl-2,2-dimethyl-cyclohexanol

2,2-dimethyl-cyclohexanone

2-Methylcyclohexanone

6-Methyl-hept-5-en-2-on

Downstream raw materials:

3-Methoxy-8,8-dimethyl-4a,4b,5,6,7,8,10,10a-octahydro-phenanthrene-1,4-dione

(4aR,5R,6E,9E)-5-(2,5-dimethoxyphenyl)-1,1-dimethyl-2,3,4,4a,5,8-hexahydro-1H-benzo[7]annulen-6-yl pivalate

C₅₁H₇₀O₅

C₄₉H₆₂O₄

Refernces

• 1、 Buter, Jeffrey,Heijnen, Dorus,Wan, Ieng Chim,Bickelhaupt, F. Matthias,Young, David C.,Otten, Edwin,Moody, D. Branch,Minnaard, Adriaan J.. "Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; A Virulence Factor of Mycobacterium tuberculosis". supporting information. p. 6686 - 6696. Retrieved 2016/08/16.
• 2、 Zhang, Jie,Li, Liqi,Wang, Yongxiang,Wang, Wenjing,Xue, Jijun,Li, Ying. "A novel, facile approach to frondosin B and 5-epi-liphagal via a new [4 + 3]-cycloaddition". supporting information. p. 4528 - 4530. Retrieved 2012/11/07.