1233250-61-7

Basic information

• Product Name: (3S,3aR,6aS,SS)-3-ethoxy-6a[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
• Synonyms: (3S,3aR,6aS,SS)-3-ethoxy-6a[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
• CAS NO: 1233250-61-7
• Molecular Weight: 460.572
• Mol File: 1233250-61-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,3aR,6aS,SS)-3-ethoxy-6a[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,6aS,SS)-3-ethoxy-6a[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one(1233250-61-7)
• EPA Substance Registry System: (3S,3aR,6aS,SS)-3-ethoxy-6a[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one(1233250-61-7)

Safety Data

• Hazardous Substances Data: 1233250-61-7(Hazardous Substances Data)

Upstream product

• 16192-08-8 p-tolylsulfonylallene 
• 149035-06-3 (S₅,S_S)-5-ethoxy-3-(p-tolylsulfinyl)furan-2(5H)-one 
• 16192-07-7 4-tosylacetonitrile 

Downstream Products

• 1233250-65-1 (3S,3aR,6aR)-3-ethoxy-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one 

Relevant articles and documents

Abnormal behaviour of allenylsulfones under Lu's reaction conditions: Synthesis of enantiopure polyfunctionalised cyclopentenes

Formal [3+2] cycloadditions of 5-alkoxyfuran-2(5H)-ones 1 and 2 with allenylsulfones 3-5, promoted by different nucleophiles, afford 3-alkoxy5-arylsulfonyl-3,3 a,6,6 a-tetrahydro-1Hcyclopenta[c]furan-l-ones in good yields with complete control of both regio- and π-facial selectivity. The incorporation of a sulfinyl group on the furanone ring enhances the reactivity of the furanones and allows the synthesis of optically pure, bicyclic adducts in good yields. Allenylsulfones evolve through a different mechanism to that proposed for allenoates (Lu's reaction) and afford bicyclic adducts in which the sulfonyl group is joined to C-5. This has advantages on the stereochemical control of further reactions leading to enantiomerically pure polyfunctionalised cyclopentenes and cyclopentanes.