174291-26-0

Basic information

• Product Name: (1R,2S,3S,4S)-1,7,7-Trimethyl-3-methylsulfanyl-bicyclo[2.2.1]heptan-2-ol
• CAS NO: 174291-26-0
• Molecular Weight: 200.345
• Mol File: 174291-26-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,3S,4S)-1,7,7-Trimethyl-3-methylsulfanyl-bicyclo[2.2.1]heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3S,4S)-1,7,7-Trimethyl-3-methylsulfanyl-bicyclo[2.2.1]heptan-2-ol(174291-26-0)
• EPA Substance Registry System: (1R,2S,3S,4S)-1,7,7-Trimethyl-3-methylsulfanyl-bicyclo[2.2.1]heptan-2-ol(174291-26-0)

Safety Data

• Hazardous Substances Data: 174291-26-0(Hazardous Substances Data)

Downstream Products

• 62137-66-0 (2R,3R)-2-(4-chlorophenyl)-3-phenyl oxirane 
• 28291-10-3 trans-(2S,3S)-2-(4-chlorophenyl)-3-phenyloxirane 

Relevant articles and documents

Highly Stereoselective Ylide Aziridination of N-Sulfonylimines with Sulfonium Propargylides: A Simple Way to Synthesize Scalemic Acetylenylaziridines

Under phase-transfer or low-temperature conditions, the ylide generated from diphenylsulfonium salt 2 readily reacts with N-sulfonylimines 1 to give acetylenylaziridines in excellent yields, but low to moderate cis/trans selectivity. When using n-BuLi as the base to generate the ylide at low termperature, product 3 with an intact silyl protecting group is obtained. t-BuOK, however, leads to desilylation product 4. With Cs2CO3 as the base, dimethylsulfonium salts 6, 21, and 22 show much better cis/trans selectivity (>98:2) than diphenylsulfonium salt 2. The asymmetric version of the above aziridination reaction using camphor-derived sulfonium salts 12-14 and 20 gives chiral aziridines with ee values up to 85percent. Both (2R,3S)-(-)-3 and (2S,3A)-(+)-3 can be prepared from 12/20 or 13/14, respectively. Ylides produced from telluronium salt 7 failed to react with imine la at room temperature, but the reaction succeeded at low temperature. Arsonium ylides from 8 cannot react with N-sulfonylimines under both sets of conditions.