1378383-75-5

Basic information

• Product Name: (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one
• Synonyms: (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one
• CAS NO: 1378383-75-5
• Molecular Weight: 338.35
• Mol File: 1378383-75-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one(1378383-75-5)
• EPA Substance Registry System: (E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one(1378383-75-5)

Safety Data

• Hazardous Substances Data: 1378383-75-5(Hazardous Substances Data)

Upstream product

• 188429-64-3 2,2,2-trifluoro-N,N,N',N'-tetramethylethane-1,1-diamine 

Downstream Products

• 1378428-01-3 (1S,2S,3S,4R)-[2-((S)-p-tolylsulfinyl)phenyl]{3-(trifluoromethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl}methanone 
• 1378427-99-6 (1S,2S,3R,4S)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone 
• 1378427-97-4 (1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone 

Relevant articles and documents

Remote stereocontrol by the sulfinyl group. Diels-Alder reaction of cyclopentadiene with substituted (S)-[2-(p-tolylsulfinyl)styrenes and (S)-[2-(p-tolylsulfinyl)phenyl] vinyl ketones

The ability of a homochiral sulfinyl group at the dienophile to act as a remote stereocontrol inductor in the Diels-Alder reaction with cyclopentadiene has been evaluated. High pressure conditions were required for the reactions of (S)-2-(p-tolylsulfinyl)styrenes 3-5 (E-1,2-disubstituted double bond) and 6-8 (1,1-disubstituted double bond). A good facial selectivity and total endo selectivity were attained with 1,1-disubstitued dienophiles, though the 1,2-disubstituted ones afforded poorer results. In contrast, (S)-[2-(p-tolylsulfinyl)phenyl] vinyl ketones 9-11 reacted readily at low temperature (-40 °C) with complete endo selectivity and high facial selectivity in the presence of Yb(OTf)3 as a chelating reagent of sulfinyl and carbonyl oxygen atoms. Concerning furan reactions, β-trifluoromethyl enone 14 afforded Diels-Alder adducts with high facial selectivity in the presence of the Lewis acid, but β-non-substituted enones 9 and 12 yielded products of furan conjugate addition to the double bond.