191861-60-6

Basic information

• Product Name: (1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane
• Synonyms: (1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane
• CAS NO: 191861-60-6
• Molecular Weight: 278.415
• Mol File: 191861-60-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane(191861-60-6)
• EPA Substance Registry System: (1S,4R,5R)-3-Benzenesulfonyl-1-isopropyl-4-methyl-bicyclo[3.1.0]hexane(191861-60-6)

Safety Data

• Hazardous Substances Data: 191861-60-6(Hazardous Substances Data)

Upstream product

• 191861-57-1 Carbonic acid (R)-5,5-bis-benzenesulfonyl-6-methyl-oct-7-en-2-ynyl ester methyl ester 
• 191861-58-2 (1R,4R,5R)-3,3-Bis-benzenesulfonyl-1-isopropenyl-4-methyl-bicyclo[3.1.0]hexane 
• 191861-56-0 (3R)-4,4-bis(phenylsulfonyl)-3-methylbut-1-ene 
• 191861-55-9 ((E)-(R)-4,4-Bis-benzenesulfonyl-3-methyl-but-1-enyl)-trimethyl-silane 

Downstream Products

• 1125-12-8 (-)-α-thujone 

Relevant articles and documents

Palladium-Catalysed Intramolecular Cyclisation of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically pure (-)-α-Thujone

Intramolecular [Pd2(dba)3]/tri(2-furyl)phosphine-catalysed (dba = dibenzylideneacetone, PhCH= CHCOCH=CHPh) cyclisations of olefinic propargylic carbonates I provided alk-1-enyl-(3-aza)bicyclo[3.1.0]-hexanes VIII in good yields. A palladium cascade sequence I → II → III → IV → VII → VIII is proposed. Furthermore, chiral propargylic carbonates such as 23, 24 and 25 allowed diastereoselective formation of bicyclo[3.1.0]hexanes 29, 30 and 31, respectively. The first diastereoselective synthesis of the monoterpene, (-)-α-thujone 40 illustrates the potential of the method.