105064-21-9

Basic information

• Product Name: (2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene
• Synonyms: (2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene
• CAS NO: 105064-21-9
• Molecular Weight: 280.345
• Mol File: 105064-21-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene(105064-21-9)
• EPA Substance Registry System: (2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene(105064-21-9)

Safety Data

• Hazardous Substances Data: 105064-21-9(Hazardous Substances Data)

Upstream product

• 931-59-9 benzenesulfenyl chloride 
• 60034-64-2 trans-4-chloro-5-(phenylsulfonyl)-2-cyclopentene 
• 105064-19-5 trans-4-chloro-cis-2,3-dihydroxy-5-(phenylsulfonyl)-2-cyclopentane 
• 60034-57-3 1-chloro-2-(phenylsulfenyl)cyclopenta-2,4-diene 
• 110890-43-2 (1S,2R,4S)-4-Benzenesulfonyl-4-phenylsulfanyl-cyclopentane-1,2-diol 
• 110890-38-5 1-phenylthio-1-phenylsulfonyl-3-cyclopentene 
• 15296-86-3 1-(phenylsulfanyl)methyl phenyl sulfone 
• 110890-44-3 1-phenylthio-1-phenylsulfonyl-(3,4-isopropylidenedioxy)cyclopentane 
• 105064-20-8 4-chloro-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)cyclopentane 
• 108-98-5 thiophenol 

Downstream Products

• 105064-23-1 (2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane 
• 113668-83-0 1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane 
• 38750-57-1 (±)-cephalotaxinone 
• 38848-21-4 (±)-cephalotaxine 
• 112177-37-4 (2S,3R,4R,5S)-(racemic)-5-(deuterophenylsulfonyl)-4-(6-(2-ethyl-t-butyldimethylsilylether)-3,4-methylenedioxyphenyl)-2,3-(isopropylidenedioxy)-5-(2-propenyl)cyclopentane 

Relevant articles and documents

Rapid Access to a Series of Highly Functionalized α,β-Unsaturated Cyclopentenones. A Caveat on Aminospirocyclization

Conjugate addition of a series of functionalized aryllithium reagents to cyclopentenyl sulfones 9 and 17 results in α-sulfonyl anion intermediates taht are further alkylated to afford triply converged adducts 12a-c and 19.Refunctionalization of these adducts provides α,β-unsaturated cyclopentenones 4a-c and 21 in high overall yields.Attempted intramolecular Michael addition of these (γ-aminopropyl)cyclopentenones to produce the spiro ring system was unsuccessful.

EFFECIENT 4 + 1 SYNTHESES OF HIGHLY FUNCTIONALIZED CYCLOPENTENES

Condensation of sulfone-activated methylene compounds with cis-1,4-dichloro-2-butene yields cyclopentenes.Elaboration of these cyclopentene products into highly functionalized intermediates is described.