3-methyl-2-methylenecyclohexanone

Base Information

• Chemical Name: 3-methyl-2-methylenecyclohexanone
• CAS No.: 73825-14-6
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.183
• Mol file: 73825-14-6.mol

Synonyms:3-methyl-2-methylenecyclohexanone

Chemical Property of 3-methyl-2-methylenecyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-2-methylenecyclohexanone

There total 5 articles about 3-methyl-2-methylenecyclohexanone 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: 67.0%

2-hydroxymethyl-3-methylcyclohexanone (78074-13-2) → 3-methyl-2-methylenecyclohexanone (73825-14-6)

Guidance literature:

With copper(I) chloride; dicyclohexyl-carbodiimide; In diethyl ether; for 2.5h; Heating;

DOI:10.1021/jo034281f

Reference yield:

2-(nitromethyl)-cyclohex-1-ene-3-one (113526-04-8) → (R)-3-Methyl-2-methylene-cyclohexanone (73825-14-6,124482-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / acetonitrile / 1 h / 25 °C

2: 1) LiBr / 1) THF, 25 deg C, 10 min, 2) -90 deg C to 0 deg C, 1 h

With lithium bromide; In acetonitrile;

DOI:10.1021/jo00044a026

Reference yield:

2-(phenylselanyl)cyclohex-2-en-1-one (57204-95-2) → 3-methyl-2-methylenecyclohexanone (73825-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2) R'X / 1) Et₂O, -20 deg C 2) Et₂O, THF, HMPA, 25 deg C

2: 1) O3 2) Et2NH / 2) CH2Cl2, Δ

With ozone; diethylamine;

DOI:10.1021/jo01301a046

upstream raw materials:

(S)-2,3-Dimethyl-2-phenylselanyl-cyclohexanone

2-hydroxymethyl-3-methylcyclohexanone

2-(phenylselanyl)cyclohex-2-en-1-one

2-(nitromethyl)-cyclohex-1-ene-3-one

Downstream raw materials:

(2R,5S,10S)-6,10-Dimethyl-spiro[4.5]dec-6-ene-2-carboxylic acid methyl ester

(2RS,5SR,10SR)-hinesol

2,3-dimethylcyclohex-2-en-1-one

Refernces

• 1、 Tamura, Rui,Watabe, Ken-ichiro,Ono, Noboru,Yamamoto, Yukio. "Asymmetric Synthesis of 3-Substituted 2-exo-Methylenealkanones by Addition-Elimination Reaction Using a Chiral Leaving Group and Organometallic Nucleophiles". . p. 4895 - 4903. Retrieved 2007/10/02.