180406-45-5

Basic information

• Product Name: (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene
• Synonyms: (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene
• CAS NO: 180406-45-5
• Molecular Weight: 365.569
• Mol File: 180406-45-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(180406-45-5)
• EPA Substance Registry System: (1R,5S)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(180406-45-5)

Safety Data

• Hazardous Substances Data: 180406-45-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 72761-60-5 9-azabicyclo<3.3.1>nonan-3-one hydrochloride 
• 75-77-4 chloro-trimethyl-silane 
• 180406-57-9 N-p-tolylsulfonyl-9-azabicyclo<3.3.1>nonan-3-one 

Downstream Products

• 180580-52-3 (1R,2R,3R,4S,6S)-3-Methyl-10-(toluene-4-sulfonyl)-4-trimethylsilanyloxy-10-aza-tricyclo[4.3.1.0^2,4]decane 
• 180406-51-3 (1R,2R,3S,4S,6S)-3-Methyl-10-(toluene-4-sulfonyl)-4-trimethylsilanyloxy-10-aza-tricyclo[4.3.1.0^2,4]decane 
• 180406-52-4 (1R,2R,3S,4S,6S)-4-hydroxy-3-methyl-N-(p-tolylsulfonyl)-10-azatricyclo<4.3.1.0^2,4>decane 
• 180406-53-5 methyl (2R,6S)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 
• 180406-54-6 (2R,6S)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 117941-17-0 (2R,6R)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 501-02-0 (-)-pinidine 

Relevant articles and documents

Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.