4-Allyl-4-methylcyclohex-2-enone

Base Information

• Chemical Name: 4-Allyl-4-methylcyclohex-2-enone
• CAS No.: 13481-16-8
• Molecular Formula: C10H14O
• Molecular Weight: 150.221
• DSSTox Substance ID: DTXSID30513719
• Mol file: 13481-16-8.mol

Synonyms:4-allyl-4-methylcyclohex-2-enone;13481-16-8;4-methyl-4-prop-2-enylcyclohex-2-en-1-one;2-Cyclohexen-1-one, 4-methyl-4-(2-propenyl)-;DTXSID30513719;4-allyl-4-methylcyclohex-2-en-1-one;AKOS032961345;F20833;4-Methyl-4-(prop-2-en-1-yl)cyclohex-2-en-1-one;J-514289

Chemical Property of 4-Allyl-4-methylcyclohex-2-enone

Chemical Property:

• PSA: 17.07000
• LogP: 2.48790
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(=O)C=C1)CC=C

Technology Process of 4-Allyl-4-methylcyclohex-2-enone

There total 8 articles about 4-Allyl-4-methylcyclohex-2-enone 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: 90.0%

C12H18O2 → 4-methyl-4-(prop-2-enyl)cyclohex-2-en-1-one (13481-16-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/cjoc.202100001

Reference yield:

2-methyl-4-pentenal (5187-71-3) + methyl vinyl ketone (78-94-4,25038-87-3) → 4-methyl-4-(prop-2-enyl)cyclohex-2-en-1-one (13481-16-8)

Guidance literature:

Multistep reaction; (i) pyrrolidine, (ii) /BRN= 506021/, (iii) aq. AcOH;

DOI:10.1002/hlca.19750580517

Reference yield:

3-Ethoxycyclohex-2-en-1-one (5323-87-5) → 4-methyl-4-(prop-2-enyl)cyclohex-2-en-1-one (13481-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 6 h / -60 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / 25 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1002/cjoc.202100001

upstream raw materials:

2-methyl-4-pentenal

methyl vinyl ketone

6-methyl-3-<(1-methylpropyl)oxy>-6-(2-propenyl)-2-cyclohexen-1-one

3-<(1-methylpropyl)oxy>-2-cyclohexen-1-one

Downstream raw materials:

methyl 5-methyl-2-oxo-5-(2-propenyl)-3-cyclohexene-1-carboxylate

4-methyl-4-(2-propenyl)cyclohexanone

4-Allyl-4-methyl-cyclohex-2-en-1-ol

2-Allyl-4-methylcyclohex-3-en-1-on

Refernces

• 1、 Bistoni, Giovanni,Das, Sayantani,De, Chandra Kanta,Ghosh, Santanu,Leutzsch, Markus,List, Benjamin,Neese, Frank,Yepes, Diana. "Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene". supporting information. p. 12347 - 12351. Retrieved 2020/03/23.