(S)-3-Phenylcyclohexanone

Base Information

• Chemical Name: (S)-3-Phenylcyclohexanone
• CAS No.: 57344-86-2
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• DSSTox Substance ID: DTXSID70455740
• Nikkaji Number: J971.390E
• Wikidata: Q76416674
• Mol file: 57344-86-2.mol

Synonyms:(S)-3-Phenylcyclohexanone;57344-86-2;(S)-3-PHENYL-CYCLOHEXANONE;(3S)-3-PHENYLCYCLOHEXAN-1-ONE;Cyclohexanone, 3-phenyl-, (3S)-;SCHEMBL714527;(S)-3-phenylcyclohexan-1-one;EX-A7802G;DTXSID70455740;CJAUDSQXFVZPTO-NSHDSACASA-N;MFCD08276411;AKOS015840423;AS-58532;PD163265;CS-0341759;P1500;T72643;A869710

Chemical Property of (S)-3-Phenylcyclohexanone

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 22 °C
• Refractive Index: -20 ° (C=1, CHCl3)
• Boiling Point: 294.012°C at 760 mmHg
• Flash Point: 123.664°C
• PSA: 17.07000
• Density: 1.043g/cm³
• LogP: 2.91330
• Storage Temp.: Refrigerator
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-3-Phenylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC(=O)C1)C2=CC=CC=C2
• Isomeric SMILES: C1C[C@@H](CC(=O)C1)C2=CC=CC=C2

Technology Process of (S)-3-Phenylcyclohexanone

There total 127 articles about (S)-3-Phenylcyclohexanone 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%

cyclohexenone (930-68-7) + phenylboronic acid (98-80-6) → (R)-3-phenylcyclohexanone (20795-53-3,57344-86-2,113829-97-3,34993-51-6)

Guidance literature:

[Rh(cyclooctadiene)2](PF₆); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In water; toluene; for 3h; Heating;

DOI:10.1016/S0040-4039(02)01288-1

Reference yield: 100.0%

cyclohexenone (930-68-7) + phenylboronic acid (98-80-6) → (S)-3-phenylcyclohexanone (57344-86-2)

Guidance literature:

cyclohexenone; phenylboronic acid; With potassium tert-butylate; bis(ethylene)rhodium acetylacetonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; 1,4-dioxane;

With water; In tetrahydrofuran; 1,4-dioxane; at 100 ℃; for 5h;

DOI:10.1002/ejic.200500254

Reference yield: 99.0%

3-phenylcyclohex-2-enone (10345-87-6) → (S)-3-phenylcyclohexanone (57344-86-2)

Guidance literature:

3-phenylcyclohex-2-enone; C₉H₁₉NO₂*C₅₀H₅₇O₄P; In dibutyl ether; at 60 ℃; for 0.0333333 - 0.0833333h;

With C₁₅H₂₃NO₄; In dibutyl ether; at 60 ℃; for 48h; Product distribution / selectivity;

upstream raw materials:

cyclohexenone

(4S)-1-methyl-4,5,6,7-tetrahydro-4-phenyl-2,1-benzisoxazolin-3-one

phenyllithium

dimethylacetal of cyclohexenone

Downstream raw materials:

(S)-3-phenylcyclohexanone-2,2,6,6-d

C₁₃H₁₉N

(1S,3R)-3-phenyl-cyclohexanecarboxylic acid amide

C₁₃H₁₅N

Refernces

• 1、 Enomoto, Yuuki,Ichiryu, Hiroki,Hu, Hao,Ura, Yasuyuki,Ogasawara, Masamichi. "C1-Symmetric Binap Derivative Featuring Single Diferrocenylphosphino-Donor Moiety". supporting information. p. 1020 - 1024. Retrieved 2021/05/07.
• 2、 Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu. "Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?". supporting information. p. 933 - 936. Retrieved 2021/03/03.