34281-94-2

Basic information

• Product Name: (2S)-2α-Phenylcyclohexanone
• Synonyms: (2S)-2α-Phenylcyclohexanone
• CAS NO: 34281-94-2
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.242
• Mol File: 34281-94-2.mol
• Article Data: 76

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S)-2α-Phenylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2α-Phenylcyclohexanone(34281-94-2)
• EPA Substance Registry System: (2S)-2α-Phenylcyclohexanone(34281-94-2)

Safety Data

• Hazardous Substances Data: 34281-94-2(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 5775-13-3 2-chloro-2-phenylcyclohexan-1-one 
• 53723-93-6 2-phenyl-1-(trimethylsiloxy)cyclohex-1-ene 
• 36103-31-8 3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl acetate 
• 591-50-4 iodobenzene 
• 145343-94-8 (R)-2-iodo-2-cyclohexen-1-yl acetate 
• 4556-09-6 2-phenylcyclohex-2-enone 
• 2362-61-0 trans-2-Phenylcyclohexanol 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 98-80-6 phenylboronic acid 
• 930-68-7 cyclohexenone 
• 33993-53-2 N,S-dimethyl-S-phenylsulfoximine 
• 214282-73-2 tert-butyldimethyl((1,4,5,6-tetrahydro[1,1'-biphenyl]-2-yl)oxy)silane 

Downstream Products

• 595604-77-6 trans-1-(2-furyl)-2-phenyl-cyclohexanol 
• 17540-18-0 (1S,2S)-cis-2-phenyl-1-cyclohexanol 
• 34281-93-1 (R)-2-phenylcyclohexanone 
• 167476-33-7 2-phenyl-1-(tert-butyldimethylsilyloxy)cyclohex-1-ene 
• 1296196-39-8 (S)-2-(1-methyl-2-(2-phenylcyclohexylidene)hydrazinyl)pyridine 
• 1296196-38-7 (S)-2-(1-methyl-2-(2-phenylcyclohexylidene)hydrazinyl)pyridine 
• 595604-83-4 (1S,2S)-1-[Hydroxy-((1R,2S,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methyl]-2-phenyl-cyclohexanol 
• 595604-80-1 C₂₁H₂₂O₃ 
• 291749-77-4 (1S,5'S,6'R)-5',6'-dihydroxybicyclohexyl-1',3'-dien-2-one 
• 98919-68-7 (1R,2S)-trans-2-phenylcyclohexanol 

Relevant articles and documents

The Silicon-Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

We have recently reported the strong and confined, chiral acid-catalyzed asymmetric 'silicon-hydrogen exchange reaction'. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes

The use of chiral enol silanes in fundamental transformations such as Mukaiyama aldol, Michael, and Mannich reactions as well as Saegusa-Ito dehydrogenations has enabled the chemical synthesis of enantiopure natural products and valuable pharmaceuticals. However, accessing these intermediates in high enantiopurity has generally required the use of either stoichiometric chiral precursors or stoichiometric chiral reagents. We now describe a catalytic approach in which strongly acidic and confined imidodiphosphorimidates (IDPi) catalyze highly enantioselective interconversions of ketones and enol silanes. These "silicon-hydrogen exchange reactions"enable access to enantiopure enol silanes via tautomerizing σ-bond metatheses, either in a deprotosilylative desymmetrization of ketones with allyl silanes as the silicon source or in a protodesilylative kinetic resolution of racemic enol silanes with a carboxylic acid as the silyl acceptor.

Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi's Catalyst

A method for safe and scalable aerobic alcohol oxidation using 2-azaadamantan-2-ol (AZADOL), an azaadamantane-type hydroxylamine catalyst, with a NOx cocatalyst in a conventional batch reactor has been developed. The use of 2 mol % AZADOL and 10 mol % NaNO2 was determined to promote aerobic alcohol oxidation quantitatively within a reasonable time (8 h). Safety is ensured by controlling the reaction temperature below the flash point of the acetic acid solvent. The robustness of the developed method is demonstrated by the 500 g scale oxidation of diacetone fructose into Shi's catalyst for asymmetric epoxidation.