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-(2-phenylsulfanyl-ethyl)-cyclohex-2-enone

3-[2-(2-aminophenylsulfanyl)ethyl]cyclohex-2-enone

Refernces

• 1、 Tsuchimochi, Izuru,Hori, Shuhei,Takeuchi, Yasuo,Egi, Masahiro,Satoh, Tomo-O,Kanomata, Kyohei,Ikawa, Takashi,Akai, Shuji. "Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction". supporting information. p. 822 - 828. Retrieved 2021/02/16.
• 2、 Brenna, Elisabetta,Crotti, Michele,De Pieri, Matteo,Gatti, Francesco G.,Manenti, Gabriele,Monti, Daniela. "Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process". . p. 3677 - 3686. Retrieved 2018/06/04.