180580-54-5

Basic information

• Product Name: (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene
• Synonyms: (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene
• CAS NO: 180580-54-5
• Molecular Weight: 365.569
• Mol File: 180580-54-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(180580-54-5)
• EPA Substance Registry System: (1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene(180580-54-5)

Safety Data

• Hazardous Substances Data: 180580-54-5(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 225089-40-7 (1S,2S,3R,4R,6R)-4-hydroxy-3-methyl-N-(p-tolylsulfonyl)-10-azatricyclo<4.3.1.0^2,4>decane 
• 225089-42-9 methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 
• 225089-43-0 (2S,6R)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 
• 118015-63-7 (2S,6S)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine 

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.