1-Methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene

Base Information

• Chemical Name: 1-Methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene
• CAS No.: 69392-27-4
• Molecular Formula: C11H16
• Molecular Weight: 148.248
• DSSTox Substance ID: DTXSID10498939
• Nikkaji Number: J637.300C
• Mol file: 69392-27-4.mol

Synonyms:69392-27-4;1-methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene;DTXSID10498939;4-isopropenyl-1-methyl-6-methylene-1-cyclohexene;1-Methyl-6-methylidene-4-(prop-1-en-2-yl)cyclohex-1-ene

Chemical Property of 1-Methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 148.125200510
• Heavy Atom Count: 11
• Complexity: 218

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(CC1=C)C(=C)C

Technology Process of 1-Methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene

There total 8 articles about 1-Methyl-6-methylidene-4-prop-1-en-2-ylcyclohexene 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: 71.0%

Acetic acid 5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl ester (344884-15-7) → 5-isopropenyl-2-methyl-3-methylene-1-cyclohexene (69392-27-4)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; molybdenum hexacarbonyl; In toluene; for 20h; Heating;

DOI:10.1016/S0040-4039(00)85945-6

Reference yield: 52.0%

C14H26OSi → C14H24OSi + 1-methyl-6-methylene-4-(prop-1-en-2-yl)cyclohex-1-ene (69392-27-4)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 24 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja307497h

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → C14H24OSi + 1-methyl-6-methylene-4-(prop-1-en-2-yl)cyclohex-1-ene (69392-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cerium(III) chloride / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: dipyridinium dichromate / dichloromethane / 1 h / 24 °C / Inert atmosphere; Molecular sieve

With dipyridinium dichromate; cerium(III) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja307497h

upstream raw materials:

Acetic acid 5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl ester

methyl magnesium iodide

diethyl ether

(S)-p-mentha-6,8-dien-2-one

Refernces

• 1、 Vyglazov,Chuiko,Izotova. "Conversions of allyl ethers in a superbasic medium". . p. 933 - 939. Retrieved 2007/10/03.