1082605-47-7

Basic information

• Product Name: (3S,1′R,4″S)-1-benzyl-3-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione
• Synonyms: (3S,1′R,4″S)-1-benzyl-3-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione
• CAS NO: 1082605-47-7
• Molecular Weight: 331.479
• Mol File: 1082605-47-7.mol

Chemical Properties

• CAS DataBase Reference: (3S,1′R,4″S)-1-benzyl-3-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,1′R,4″S)-1-benzyl-3-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione(1082605-47-7)
• EPA Substance Registry System: (3S,1′R,4″S)-1-benzyl-3-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione(1082605-47-7)

Safety Data

• Hazardous Substances Data: 1082605-47-7(Hazardous Substances Data)

Upstream product

• 1082605-46-6 (S,Z)-4-(2,3-dibromoprop-1-enyl)-2,2-dimethyl-1,3-dioxolane 
• 1082605-45-5 (S,Z)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 182969-96-6 (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate 
• 80532-35-0 (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 91926-90-8 ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 79060-23-4 (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 64520-58-7 ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 17642-88-5 1-benzyl-2-pyrrolidinethione 
• 569349-87-7 (4S)-4-[(1Z)-3-bromoprop-1-enyl]-2,2-dimethyl-1,3-dioxolane 
• 198402-59-4 (S,E)-4-(3-bromoprop-1-en-1-yl)-2,2-dimethyl-1,3-dioxolane 
• 1082605-48-8 (3S,1′R,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione 

Downstream Products

• 1082605-56-8 (3S,3'R,4'S)-1-benzyl-3-(4,5-dihydroxypent-1-en-3-yl)pyrrolidine-2-thione 
• 1082605-54-6 (3S,1'R)-1-benzyl-3-(1-hydroxymethylallyl)pyrrolidine-2-thione 

Relevant articles and documents

Reversal of facial selectivity in a thia-Claisen rearrangement by incorporation of a vinylic bromine substituent

Thia-Claisen rearrangements have been carried out using N-benzylpyrrolidine-2-thione and chiral allylic bromides derived from d-mannitol. Introduction of a bromine atom onto the double bond of the allylic bromide reverses the sense of diastereoselectivity in the [3,3]-sigmatropic rearrangement. Density functional theory calculations lead us to rationalise the observed selectivity in terms of a Cieplak effect.

Diastereoselective Thia-Claisen rearrangement of pyrrolidinone-derived ketene N,S-acetals

Thia-Claisen rearrangements of S-allylic ketene N,S-acetals were carried out using substrates with an external allylic stereogenic centre. High levels of diastereoselectivity were observed only when a bromine substituent was introduced onto the double bon