Cyclohexanone, 2-(phenylmethyl)-, (S)-

Base Information

• Chemical Name: Cyclohexanone, 2-(phenylmethyl)-, (S)-
• CAS No.: 59919-09-4
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.269
• DSSTox Substance ID: DTXSID30426411
• Nikkaji Number: J624.547A
• Mol file: 59919-09-4.mol

Synonyms:(S)-2-Benzylcyclohexanone;Cyclohexanone, 2-(phenylmethyl)-, (S)-;59919-09-4;SCHEMBL9790769;DTXSID30426411

Chemical Property of Cyclohexanone, 2-(phenylmethyl)-, (S)-

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 188.120115130
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)CC2=CC=CC=C2
• Isomeric SMILES: C1CCC(=O)[C@@H](C1)CC2=CC=CC=C2

Technology Process of Cyclohexanone, 2-(phenylmethyl)-, (S)-

There total 83 articles about Cyclohexanone, 2-(phenylmethyl)-, (S)- 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: 99.0%

(E)-2-benzylidenecyclohexanone (5682-83-7,31021-02-0,1467-15-8) → (R)-2-benzylcyclohexanone (946-33-8,59919-09-4,77857-39-7,91603-45-1)

Guidance literature:

With C₂₄BF₂₀^(1-)*C₃₄H₃₆IrNPS⁽¹⁺⁾; hydrogen; In dichloromethane; at 20 ℃; for 16h; under 15001.5 Torr; enantioselective reaction;

DOI:10.1021/acs.orglett.0c04012

Reference yield: 92.0%

2-Benzylidenecyclohexanone (5682-83-7) → (R)-2-benzylcyclohexanone (946-33-8,59919-09-4,77857-39-7,91603-45-1)

Guidance literature:

With C₃₂H₁₂BF₂₄^(1-)*C₄₆H₅₄IrNO₄PS⁽¹⁺⁾; hydrogen; In dichloromethane; at 20 ℃; for 18h; under 37503.8 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.joc.9b00829

Reference yield: 90.0%

(2R)-2-benzylcyclohexanol → (R)-2-benzylcyclohexanone (946-33-8,59919-09-4,77857-39-7,91603-45-1)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; bathophenanthroline; caesium carbonate; copper(l) chloride; In toluene; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2012.08.095

upstream raw materials:

[(S)-2-Benzyl-cyclohex-(Z)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine

1-(Trimethylsilyloxy)cyclohexene

cyclohexanone

benzyl bromide

Downstream raw materials:

(1S,2S)-α-benzylcyclohexanol

(R)-7-benzyloxacycloheptan-2-one

(2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carboxylic acid

Refernces

• 1、 Peters, Bram B. C.,Jongcharoenkamol, Jira,Krajangsri, Suppachai,Andersson, Pher G.. "Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones". supporting information. p. 242 - 246. Retrieved 2021/01/13.
• 2、 Yang, Jiaxin,Li, Xiuxiu,You, Cai,Li, Shuailong,Guan, Yu-Qing,Lv, Hui,Zhang, Xumu. "Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds". supporting information. p. 856 - 859. Retrieved 2020/02/15.