4-Phenyl-3-cyclohexen-1-ol

Base Information

• Chemical Name: 4-Phenyl-3-cyclohexen-1-ol
• CAS No.: 15619-51-9
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• DSSTox Substance ID: DTXSID601311232
• Nikkaji Number: J495.670B
• Mol file: 15619-51-9.mol

Synonyms:4-phenyl-3-cyclohexen-1-ol;15619-51-9;4-phenyl-cyclohex-3-en-1-ol;SCHEMBL14336997;DTXSID601311232

Chemical Property of 4-Phenyl-3-cyclohexen-1-ol

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=CCC1O)C2=CC=CC=C2

Technology Process of 4-Phenyl-3-cyclohexen-1-ol

There total 16 articles about 4-Phenyl-3-cyclohexen-1-ol 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: 65.0%

2-phenyl-2-vinylcyclobutanone (81452-67-7) → 4-hydroxy-1-phenylcyclohexene (15619-51-9)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 25 ℃; for 2h;

DOI:10.1016/S0040-4020(01)93268-5

Reference yield: 49.0%

triphenylboroxine (3262-89-3) + 4-hydroxycyclohexanone (13482-22-9) → 4-hydroxy-1-phenylcyclohexene (15619-51-9)

Guidance literature:

With tetrakis(triphenylphosphine)nickel⁽⁰⁾; water; 1,2-bis-(dicyclohexylphosphino)ethane; In diethylene glycol dimethyl ether; at 110 ℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.7b02742

Reference yield:

1-bromovinylbenzene (98-81-7) + pinacol vinylboronate (75927-49-0) → 4-hydroxy-1-phenylcyclohexene (15619-51-9) + 3-Phenyl-cyclohex-3-enol (140837-16-7)

Guidance literature:

1-bromovinylbenzene; pinacol vinylboronate; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,4-dioxane; water; at 50 ℃; for 1h; Inert atmosphere; Sealed tube;

In 1,4-dioxane; water; at 150 ℃; for 23h; Inert atmosphere; Sealed tube;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 1h; Overall yield = 62 %; Overall yield = 27.2 mg; regioselective reaction;

DOI:10.1055/s-0037-1611228

upstream raw materials:

trivinyl borane

2-phenyl-1,3-butadiene

tri-n-butyl(vinyl)tin

9-vinyl-9-borabicyclo<3.3.1>nonane

Downstream raw materials:

O-(4-Phenyl-3-cyclohexenyl-⁽¹⁾)-S-methylxanthat

1-phenyl-cyclohexa-1,3-diene

1-phenyl-1,4-cyclohexadiene