110770-73-5

Basic information

• Product Name: (1'R^*,2'E,3R^*,4S^*,S^*_S)-3-t-butoxy-4-<1'-pentyl-3'-(phenylsulfinyl)prop-2'-enyl>cyclopentanone
• Synonyms: (1'R^*,2'E,3R^*,4S^*,S^*_S)-3-t-butoxy-4-<1'-pentyl-3'-(phenylsulfinyl)prop-2'-enyl>cyclopentanone
• CAS NO: 110770-73-5
• Molecular Weight: 390.587
• Mol File: 110770-73-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1'R^*,2'E,3R^*,4S^*,S^*_S)-3-t-butoxy-4-<1'-pentyl-3'-(phenylsulfinyl)prop-2'-enyl>cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R^*,2'E,3R^*,4S^*,S^*_S)-3-t-butoxy-4-<1'-pentyl-3'-(phenylsulfinyl)prop-2'-enyl>cyclopentanone(110770-73-5)
• EPA Substance Registry System: (1'R^*,2'E,3R^*,4S^*,S^*_S)-3-t-butoxy-4-<1'-pentyl-3'-(phenylsulfinyl)prop-2'-enyl>cyclopentanone(110770-73-5)

Safety Data

• Hazardous Substances Data: 110770-73-5(Hazardous Substances Data)

Upstream product

• 56561-12-7 (E)-1-(phenylsulfinyl)oct-2-ene 
• 73448-15-4 4-tert-butoxycyclopent-2-en-1-one 
• 84019-03-4 1-phenylthio-2-octene 
• 84019-04-5 1-(phenylsulfinyl)oct-2-ene 

Relevant articles and documents

Aprotic Conjugate Addition of Allyllithium Reagents Bearing Polar Groups to Cyclic Enones. 1. 3-Alkylallyl Systems

The conjugate addition of lithiated (E)- and (Z)-oct-2-enyl sulfoxides and phosphine oxides, but-2-enyl sulfoxides, phosphine oxides and phosphonates, and 3,3-dimethylallyl and allyl sulfoxides to cyclic enones has been examined.The E and Z carbanions react in highly diastereoselective fashion with five-membered cyclic enones to deliver respectively syn and anti vinylic sulfoxides, phosphine oxides, and phosphonates.Hexamethylphosphoric triamide has no regiochemical influence on these reactions.The regiochemical and stereochemical outcomes of these reactions are rationalized in terms of planar lithiated reagents in which Li+ is bound to oxygen attached to sulfur or phosphorus of the polar group and a 10-membered "trans-decalyl"- or "trans-fused chair-chair"-like transition-state model in which the lithiated reagent adopts an endo orientation over one face of the enone such that for the reagent, the 3-alkyl group is pseudoequatorial, and for the Z, pseudoaxial.

THE DIASTEREOSPECIFIC APROTIC CONJUGATE ADDITION REACTIONS OF CARBANIONS DERIVED FROM ALLYLIC SULFOXIDES AND ALLYLIC PHOSPHINE OXIDES.

The title carbanions undergo conjugate addition to cyclic enones in THF to deliver vinylic sulfoxides and vinylic phosphine oxides as single diastereomers.