57344-86-2

Basic information

• Product Name: (S)-3-PHENYLCYCLOHEXANONE
• Synonyms: (S)-3-Phenylcyclohexanone,99%e.e.;(S)-3-PHENYLCYCLOHEXANONE
• CAS NO: 57344-86-2
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• Product Categories: Synthetic Organic Chemistry;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral)
• Mol File: 57344-86-2.mol
• Article Data: 231

Chemical Properties

• Melting Point: 22 °C
• Boiling Point: 294.012°C at 760 mmHg
• Flash Point: 123.664°C
• Appearance: /
• Density: 1.043g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: -20 ° (C=1, CHCl3)
• Storage Temp.: Refrigerator
• CAS DataBase Reference: (S)-3-PHENYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-PHENYLCYCLOHEXANONE(57344-86-2)
• EPA Substance Registry System: (S)-3-PHENYLCYCLOHEXANONE(57344-86-2)

Safety Data

• Hazardous Substances Data: 57344-86-2(Hazardous Substances Data)

Usage

General Description

(S)-3-Phenylcyclohexanone is a chemical compound with the molecular formula C12H14O. It is an organic compound that belongs to the family of cyclohexanones, which are aromatic compounds with a six-membered carbon ring. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, as well as in the production of fragrances and flavoring agents. It is also known for its potential as a chiral auxiliary in asymmetric synthesis, due to the presence of a chiral center in its molecular structure. Additionally, (S)-3-Phenylcyclohexanone has been studied for its biological activities, particularly its potential as an anti-inflammatory and antimicrobial agent.

InChI:InChI=1/C12H14O/c13-12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2/t11-/m0/s1

Upstream product

• 930-68-7 cyclohexenone 
• 134880-11-8 (4S)-1-methyl-4,5,6,7-tetrahydro-4-phenyl-2,1-benzisoxazolin-3-one 
• 591-51-5 phenyllithium 
• 1728-18-3 dimethylacetal of cyclohexenone 
• 100-58-3 phenylmagnesium bromide 
• 115880-50-7 (R)-2-phenoxypropanoic acid methyl ester 
• 396718-95-9 [(R)-3-Phenyl-cyclohex-(E)-ylidene]-acetaldehyde 
• 1078-58-6 diphenylzinc 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 16419-60-6 2-Methylphenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 960-71-4 triphenylborane 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 76936-85-1 (+)-(R)-3-phenyl-1-(2-tolyl)cyclohexene 
• 1232059-66-3 C₁₃H₁₆O₂ 
• 1232059-68-5 (1R,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-56-1 C₁₃H₁₅N 
• 1232059-70-9 (1S,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-79-8 C₁₃H₁₉N 
• 1489231-21-1 (S)-3-phenylcyclohexanone-2,2,6,6-d 

Relevant articles and documents

Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.

Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones

Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1