107647-76-7

Basic information

• Product Name: (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol
• Synonyms: (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol
• CAS NO: 107647-76-7
• Molecular Weight: 272.368
• Mol File: 107647-76-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol(107647-76-7)
• EPA Substance Registry System: (S_S,1S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol(107647-76-7)

Safety Data

• Hazardous Substances Data: 107647-76-7(Hazardous Substances Data)

Upstream product

• 128176-10-3 p-tolyl 1-(trimethylsilyl)vinyl sulfoxide 
• 100-52-7 benzaldehyde 
• 308818-91-9 (S_S)-1-hydroxy-1-phenyl-2-(phenylselenyl)-2-(p-tolylsulfinyl)propane 
• 308818-87-3 (R_S)-1-hydroxy-1-phenyl-2-(p-tolylsulfinyl)propane 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 308818-93-1 (3S,S_S)-3-benzoyloxy-3-phenyl-2-(p-tolylsulfinyl)-1-propene 
• 107647-79-0 (S_S,1R)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-ol 
• 153123-05-8 (S_S,S)-(E)-1-phenyl-2-(p-tolylsulfinyl)-3-(trimethylsilyl)-2-propen-1-ol 
• 54828-68-1 (R)-p-tolyl vinyl sulfoxide 
• 107647-71-2 (R)_S-dimethylamino-2 p-tolylsulfinyl-1 ethane 
• 107647-73-4 3-Dimethylamino-1-phenyl-2-((R)-toluene-4-sulfinyl)-propan-1-ol 

Downstream Products

• 107647-82-5 (+)-(S)-1-phenyl-2-(p-tolylsulfinyl)-2-propen-1-one 

Relevant articles and documents

Preparation of optically pure propargylic and allylic alcohols from 2-(trimethylsilyl)vinyl sulfoxides as a chiral ethynyl anion synthon: Computational studies on elimination reaction of 2-(trimethylsilyl)vinyl sulfoxides

The reaction of the (α-carbanion derived from (trimethylsilyl)vinyl sulfoxides with aldehydes afforded a diastereomeric mixture of the products. Each diastereomer was subjected to specific elimination reactions to give optically pure propargylic, trimethylsilylated propargylic, and allylic alcohols. Acceleration of the sulfenic acid-elimination from the β-silylvinyl sulfoxide was demonstrated by the ab initio calculation to be ascribed mainly to the β-effect of the silyl group.

Stereocontrolled asymmetric synthesis of optically active acylcyclopropane derivatives by Michael additions of bromomalonate to chiral α-acylvinylic sulfoxides

Michael addition of bromomalonate carbanions to chiral α-acylvinylic sulfoxides and the subsequent intramolecular alkylation yielded optically active acylcyclopropane derivatives with high enantiomeric excess. Stereochemistry of the product was determined by chemical correlation to a compound of known absolute configuration. The mechanism for the asymmetric induction is deduced on the basis of the stereochemical results obtained.

Fluoride-catalyzed generation and reactions of 1-(p-tolylsulfinyl)vinyl anion

Fluoride-catalyzed desilylation of p-tolyl 1-(trimethylsilyl) vinyl sulfoxide in the presence of aldehydes results in modest yields of the corresponding allylic alcohols. Upon treatment with alkaline solution at 0°C it undergoes efficient protodesilylatio