114552-41-9

Basic information

• Product Name: (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one
• Synonyms: (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one
• CAS NO: 114552-41-9
• Molecular Weight: 274.427
• Mol File: 114552-41-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one(114552-41-9)
• EPA Substance Registry System: (1R)-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one(114552-41-9)

Safety Data

• Hazardous Substances Data: 114552-41-9(Hazardous Substances Data)

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 16601-01-7 benzenethiosulfonic acid S-benzyl ester 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 

Downstream Products

• 132696-66-3 (1R,2S,3R,4S)-3-((S)-(S)-2-Hydroxy-2-phenyl-ethanesulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 132609-89-3 (1R,2S,3R,4S)-3-((S)-(R)-2-Hydroxy-2-phenyl-ethanesulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 132609-88-2 (1R,2S,3R,4S)-3-((R)-2-Hydroxy-2-phenyl-ethylsulfanyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 132609-87-1 2-((S)-(1S,2R,3S,4R)-3-Hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinyl)-1-phenyl-ethanone 
• 132609-86-0 2-((1S,2R,3S,4R)-3-Hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylsulfanyl)-1-phenyl-ethanone 
• 114552-53-3 (1R,2S,S_S)-exo-3-(benzylsulfinyl)-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol 
• 1439-07-2 (S,S)-trans-stilbene oxide 
• 1439-07-2 (R,R)-trans-stilbene epoxide 
• 158809-09-7 (-)-(1R,2S)-2-methoxy-exo-3-(benzylthio)-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 22440-35-3 trans-(2R,3R)-2-(4-methylphenyl)-3-phenyl oxirane 
• 114552-49-7 (+)-(1R,2S,3R,4S)-1,7,7-Trimethyl-3-(benzylthio)bicyclo<2.2.1>heptan-2-ol 

Relevant articles and documents

Preparation of Stable, Camphor-Derived, Optically Active Allyl and Alkyl Sulfoxides and Thermal Epimerization of the Allyl Sulfoxides

(+)-Camphor is converted by thioalkylation of the lithium enolate with allyl and alkyl p-toluenethiosulfonates into exo-3-(allylthio)- and exo-3-(alkylthio)camphors, which upon reduction with diisobutylaluminum hydride give the coresponding exo-(allylthio)- and exo-(alkylthio)isoborneols.Oxidation of the sulfides with m-chloroperbenzoic acid gives the exo-(allylsulfinyl)- and exo-(alkylsulfinyl)isoborneols in a stereochemically pure state.The configuration at sulfur in the sulfoxides is determined by X-ray crystalography of the allyl derivative to be SS; this configuration implies that the exo-hydroxyl group at C2 controls the stereochemical outcome of the oxidation.The allylic sulfoxides are stable at room temperature, but upon heating through their melting points undergo a remarkable and generally quantitative rearrangement into the RS epimers.

Preparation of enantiomerically enriched (2R,3R)- or (2S,3S)-trans-2,3-diaryloxiranes via camphor-derived sulfonium ylides

Easily available D-(+)-camphor-derived sulfides 3, 4, 6, and 7 were employed for enantioselective epoxidation via an ylide route. When benzylated or methylated sulfides were used as reagents or mediators for benzylidene transfer, stoichiometric and catalytic epoxidations were realized, respectively. Opposite asymmetric induction was achieved only when sulfides containing exo- (3 and 4) and endo- (6 and 7) alkylthio groups were used. That is, both (+)- and (-)-trans-diaryloxiranes could be obtained in excellent yields and moderate to good ee values under extremely mild conditions from the same chiral pool-derived reagents. A nonbonded interaction between the free OH in the ylides from sulfides (3, 6, and 7) and the carbonyl group of aldehydes controls the approach of the substrates to the ylidic carbon preferentially at one specified face and therefore leads to a more efficient asymmetric induction than that in the case of the ylide from methyl-protected hydroxylated sulfides 4, which cannot cause such an interaction. The same opposite asymmetric induction was also observed in the catalytic reaction with methyl-protected hydroxylated sulfide 4b and unprotected hydroxylated sulfide 3b.