1-Isopropyl-4-methylenecyclohexane

Base Information

• Chemical Name: 1-Isopropyl-4-methylenecyclohexane
• CAS No.: 1124-24-9
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• DSSTox Substance ID: DTXSID70892353
• Wikidata: Q27126498
• Metabolomics Workbench ID: 60439
• Mol file: 1124-24-9.mol

Synonyms:1-isopropyl-4-methylenecyclohexane;1(7)-p-Menthene;4-isopropyl-1-methylenecyclohexane;1-(1-methylethyl)-4-methylenecyclohexane;CHEBI:59156;4-methylene-1-(propan-2-yl)cyclohexane;1124-24-9;1-methylidene-4-propan-2-ylcyclohexane;Epitope ID:123901;DTXSID70892353;AKOS011393604;1-methylene-4-(1-methylethyl)cyclohexane;1-methylidene-4-(propan-2-yl)cyclohexane;Q27126498

Chemical Property of 1-Isopropyl-4-methylenecyclohexane

Chemical Property:

• Vapor Pressure: 2.04mmHg at 25°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 138.140850574
• Heavy Atom Count: 10
• Complexity: 112

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC(=C)CC1

Technology Process of 1-Isopropyl-4-methylenecyclohexane

There total 7 articles about 1-Isopropyl-4-methylenecyclohexane 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%

4-isopropyl-cyclohexanone (5432-85-9) + Methyltriphenylphosphonium bromide (1779-49-3) → 1-methylene-4-isopropylcyclohexane (1124-24-9)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In diethyl ether; at 20 ℃; for 1h;

4-isopropyl-cyclohexanone; In diethyl ether; at 20 ℃;

DOI:10.1021/jacs.1c11343

Reference yield:

p-menth-1-ene (61585-35-1,5502-88-5,34363-01-4) → 1-methylene-4-isopropylcyclohexane (1124-24-9)

Guidance literature:

In methanol; xylene; Irradiation;

DOI:10.1021/ja00996a021

Reference yield:

4-isopropylcyclohexanone ethylene ketal → 1-methylene-4-isopropylcyclohexane (1124-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / tetrahydrofuran; water

2: n-butyllithium / diethyl ether; hexane / 0 - 20 °C

With n-butyllithium; sulfuric acid; In tetrahydrofuran; diethyl ether; hexane; water;

DOI:10.1021/acs.orglett.7b01329

upstream raw materials:

(Δ¹-Menthenyl-(7))-methanol

4-isopropyl-cyclohexanone

Methyltriphenylphosphonium bromide

p-menth-1-ene

Downstream raw materials:

(Δ¹-Menthenyl-(7))-methanol

p-menth-1-ene

(+)-p-menth-1-ene

(S)-carvomenthene

Refernces

• 1、 Mitsui,S. et al.. "-". . p. 1523 - 1530. Retrieved 1973.
• 2、 Luo, Weiwei,Lin, Lili,Zhang, Yu,Liu, Xiaohua,Feng, Xiaoming. "Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction". supporting information. p. 3374 - 3377. Retrieved 2017/07/15.