135227-12-2

Basic information

• Product Name: (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone
• Synonyms: (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone
• CAS NO: 135227-12-2
• Molecular Weight: 266.404
• Mol File: 135227-12-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone(135227-12-2)
• EPA Substance Registry System: (S)-4-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopent-2-enone(135227-12-2)

Safety Data

• Hazardous Substances Data: 135227-12-2(Hazardous Substances Data)

Upstream product

• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 
• 71242-58-5 (1S,2R,4R)-(-)-10-mercaptoisoboneol 

Relevant articles and documents

A New Resolution Procedure for the Preparation of Both (R)-(+)- and (S)-(-)-4-tert-Butoxycyclopent-2-enone from Racemic 4-tert-Butoxycyclopent-2-enone and Conversion of (R)-(+)-Butoxycyclopent-2-enone into (R)-(+)-4-Acetoxycyclopent-2-enone. A New Method for the Determination of the ...

(1S)-(-)-10-Mercaptoisoborneol undergoes conjugate addition to (+/-)-4-tert-butoxycyclopent-2-enone in methanol containing N,N,N',N'-tetramethylethylenediamine to give a 1:1 mixture of diastereomers of 3-tert-butoxy-4-heptanyl)methyl>thio>cyclopentanone in 93-95percent yield.The mixture is converted by m-chloroperbenzoic acid into the corresponding sulfoxide mixture.The (3R,4R,RS)-sulfoxide isomer, whose absolute configuration has been determined by X-ray crystallography, crystallizes cleanly from this mixture in an enantiomeric yield of 76percent from the corresponding sulfide.It is decomposed on silica gel to generate (R)-(+)-4-tert-butoxycyclopent-2-enone, with an enantiomeric purity of >/- 99.9percent in 92percent yield from the sulfoxide, and 10-thiodiisobornyl 10'-sulfoxide.Similarly, the (S)-(-)-enone is prepared from (1R)-(+)-10-mercaptoisoborneol.The (+/-) and the (R)-(+)-enone, respectively, are converted by a catalytic amount of FeCl3 in acetic anhydride into (+/-) and (R)-(+)-4-acetoxycyclopent-2-enone (with an enantiomeric purity of >/- 99.9percent) in 80percent yield.The enantiomeric purity of the products was assessed through their treatment with (-)-10-mercaptoisoborneol and analysis of the adducts by HPLC and 400-MHz 1H NMR spectroscopy.