3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one

Base Information

• Chemical Name: 3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one
• CAS No.: 17605-08-2
• Molecular Formula: C10H14O
• Molecular Weight: 150.221
• DSSTox Substance ID: DTXSID20498682
• Nikkaji Number: J1.979.858E
• Wikidata: Q82348893
• Mol file: 17605-08-2.mol

Synonyms:17605-08-2;3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one;DTXSID20498682;2-allyl-3-methylcyclohex-2-en-1-one

Chemical Property of 3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 211

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)CCC1)CC=C

Technology Process of 3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one

There total 14 articles about 3-Methyl-2-(prop-2-en-1-yl)cyclohex-2-en-1-one 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%

methyllithium (917-54-4) + 2-allyl-3-bromocyclohex-2-en-1-one (56745-18-7) → 2-allyl-3-methyl-2-cyclohexen-1-one (17605-08-2)

Guidance literature:

With copper(I) thiophenolate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 2.5h;

DOI:10.1139/v82-185

Reference yield: 74.0%

ethyl 3-allyl-2-methyl-4-oxocyclohex-2-ene-1-carboxylate (95578-22-6) → 2-allyl-3-methyl-2-cyclohexen-1-one (17605-08-2)

Guidance literature:

ethyl 3-allyl-2-methyl-4-oxocyclohex-2-ene-1-carboxylate; With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; water; at 90 ℃; for 24h;

DOI:10.1021/ol500011f

Reference yield: 74.0%

2-Iodo-3-methyl-2-cyclohexen-1-one (140710-03-8) + allyl bromide (106-95-6) → 2-allyl-3-methyl-2-cyclohexen-1-one (17605-08-2)

Guidance literature:

2-Iodo-3-methyl-2-cyclohexen-1-one; With lithium dineopentylcuprate; In tetrahydrofuran; at -78 - -30 ℃; for 3h;

allyl bromide; In tetrahydrofuran; at -30 ℃; for 0.5h;

DOI:10.1002/1521-3773(20020902)41:17<3263::AID-ANIE3263>3.0.CO;2-8

upstream raw materials:

ethyl 3-allyl-2-methyl-4-oxocyclohex-2-ene-1-carboxylate

methyl magnesium iodide

3-ethoxy-2-allylcyclohex-2-en-1-one

3-(3-butenyl)cyclohex-2-en-1-one

Downstream raw materials:

3-methyl-2-propyl-cyclohex-2-enone

3-allyl-4-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester

2-Allyl-3-methylcyclohex-2-enol

2-Allyl-1-(but-3-enyl)-cyclohex-1-en-3-on