14132-21-9

Basic information

• Product Name: Cyclohexanone, 2-(1,1-dimethylethyl)-, (2S)-
• CAS NO: 14132-21-9
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Mol File: 14132-21-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2-(1,1-dimethylethyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2-(1,1-dimethylethyl)-, (2S)-(14132-21-9)
• EPA Substance Registry System: Cyclohexanone, 2-(1,1-dimethylethyl)-, (2S)-(14132-21-9)

Safety Data

• Hazardous Substances Data: 14132-21-9(Hazardous Substances Data)

Upstream product

• 92207-91-5 C₁₈H₂₉NO₂S 
• 1728-46-7 2-tert-butylcyclohexanone 
• 33993-53-2 N,S-dimethyl-S-phenylsulfoximine 
• 557088-93-4 (+)-3β-Acetoxy-Δ⁵-aetiensaeure-trans-2-tert.-butyl-cyclohexanolester 
• 5448-22-6 trans-2-tert-butylcyclohexan-1-ol 
• 13492-06-3 (S,S)-cis-2-tert-butylcyclohexanol 
• 98104-30-4 trans 2-tert-butylcyclohexanol 
• 159425-79-3 (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 13492-06-3 (S,S)-cis-2-tert-butylcyclohexanol 
• 13492-07-4 (+)-(1S,2R)-2-(tert-butyl)cyclohexanol 
• 98104-30-4 trans 2-tert-butylcyclohexanol 

Relevant articles and documents

Chiral Sulfur Compounds. Part 25. Diastereoselective 1,2-Additions of Lithiated (+)-(S)-N-tert-Butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to Ketones

Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone.Racemic chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization.Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity.The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis.The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.

N,S-DIMETHYL-S-PHENYLSULFOXIMINE. A REAGENT FOR THE OPTICAL RESOLUTION OF KETONES

The addition of the α-lithio derivative of (+)- or (-)-N,S-dimethyl-S-phenylsulfoximine to selected dl-ketones was carried out at -78 deg C in tetrahydrofuran followed by acid quench at that temperature to produce mixtures of diastereomeric β-hydroxysulfoximines.The optically-active diastereomers were chromatographically separated on silica gel.The purified diastereomers were thermolyzed at ca. 130 deg to produce optically-active ketones and the optically-active sulfoximine which could be recycled.