3-Vinyl-cyclohex-2-enone

Base Information

• Chemical Name: 3-Vinyl-cyclohex-2-enone
• CAS No.: 40996-91-6
• Molecular Formula: C8H10O
• Molecular Weight: 122.167
• DSSTox Substance ID: DTXSID00472021
• Nikkaji Number: J845.227J
• Mol file: 40996-91-6.mol

Synonyms:3-Vinyl-cyclohex-2-enone;3-Vinyl-2-cyclohexen-1-one;40996-91-6;3-Vinylcyclohex-2-enone;SCHEMBL275931;DTXSID00472021;SYSKKMBZQQKRKI-UHFFFAOYSA-N

Chemical Property of 3-Vinyl-cyclohex-2-enone

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 165

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC1=CC(=O)CCC1

Technology Process of 3-Vinyl-cyclohex-2-enone

There total 17 articles about 3-Vinyl-cyclohex-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: 100.0%

3-Ethoxycyclohex-2-en-1-one (5323-87-5) + vinyl magnesium bromide (1826-67-1) → 3-vinyl-cyclohex-2-enone (40996-91-6)

Guidance literature:

With tert-butyl methyl ether; In tetrahydrofuran; at 0 - 20 ℃; for 1.66h;

DOI:10.1021/op500314c

Reference yield: 80.0%

1-<(tert-butyldimethylsilyl)oxy>-3-ethenyl-1-cyclohexene (98582-25-3) → 3-vinyl-cyclohex-2-enone (40996-91-6)

Guidance literature:

1-<(tert-butyldimethylsilyl)oxy>-3-ethenyl-1-cyclohexene; With (x)BF₄*C₉H₁₄NO⁽¹⁺⁾; In dichloromethane; at -78 ℃; for 1h;

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃;

DOI:10.1021/ol2029417

Reference yield: 60.0%

tri-n-butyl(vinyl)tin (7486-35-3) + 3-(trifluoromethanesulfonyloxy)-2-cyclohexen-1-one (109459-28-1) → 3-vinyl-cyclohex-2-enone (40996-91-6)

Guidance literature:

With triphenylphosphine; palladium diacetate; In tetrahydrofuran; at 55 ℃; for 1h;

DOI:10.1016/S0040-4039(00)93572-X

upstream raw materials:

3-Ethoxycyclohex-2-en-1-one

3-isobutoxycyclohex-2-en-1-one

(3-ethoxy-cyclohex-2-enyliden)-acetic acid ethyl ester

tri-n-butyl(vinyl)tin

Downstream raw materials:

3-propyl-2-cyclohexen-1-one

3-propylidenecyclohexan-1-one

3-vinyl-1-methyl-2-cyclohexen-1-ol

3-(2'-methyl-3'-trimethylsilyl-2'-cyclopentene-1'-yl)-2-cyclohexen-1-one

Refernces

A Short-Step Synthetic Approach to Eudesmane Skeleton. A Synthesis of (+/-)-β-Eudesmol and Related Eudesman Sesquiterpenes

10.1246/bcsj.61.3770

The research aims to develop an efficient and concise method for synthesizing the eudesmane skeleton, which is a significant structural motif in various sesquiterpenes, including (±)-β-eudesmol, cryptomeridiol, and neointermediol. The study employs a strategy based on the use of key intermediates like A or B, which undergo intramolecular cyclization via aldol condensation or Michael reaction. The synthesis starts from readily available 3-vinyl-2-cyclohexen-1-one, which is treated with dimethyl malonate in the presence of sodium methoxide to yield the Michael adduct. Subsequent steps involve acetalization, reduction with lithium aluminum hydride, selective benzylation, oxidation with pyridinium dichromate (PDC), and catalytic hydrogenation. The crucial step is the intramolecular aldol condensation, which constructs the desired α,β-unsaturated ketone. The final steps include oxidation, esterification, and selective reduction to obtain the target compounds. The research concludes that this approach provides a general method for constructing eudesmane sesquiterpenes, offering a formal total synthesis of (±)-β-eudesmol and its related compounds.