228717-97-3

Basic information

• Product Name: 2-(3',5'-difluorophenyl)-3-(4'-methylthiophenyl)cyclopent-2-en-1-one
• Synonyms: 2-(3',5'-difluorophenyl)-3-(4'-methylthiophenyl)cyclopent-2-en-1-one
• CAS NO: 228717-97-3
• Molecular Weight: 316.371
• Mol File: 228717-97-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(3',5'-difluorophenyl)-3-(4'-methylthiophenyl)cyclopent-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3',5'-difluorophenyl)-3-(4'-methylthiophenyl)cyclopent-2-en-1-one(228717-97-3)
• EPA Substance Registry System: 2-(3',5'-difluorophenyl)-3-(4'-methylthiophenyl)cyclopent-2-en-1-one(228717-97-3)

Safety Data

• Hazardous Substances Data: 228717-97-3(Hazardous Substances Data)

Upstream product

• 104-95-0 (4-bromophenyl)thioanisole 
• 151361-87-4 1-ethynyl-3,5-difluorobenzene 
• 461-96-1 3,5-difluorobromobenzene 
• 324529-53-5 5-bromo-5-(3,5-difluorophenyl)-1-(4-methylsulfanylphenyl)pent-4-en-1-one 
• 21573-80-8 1-(4-methylthiophenyl)propenone 
• 1442-06-4 4-(methylthio)benzoyl chloride 
• 13205-48-6 4-(methylthio)benzoic acid 
• 324529-54-6 2-(3,5-difluorophenyl)-1-(4-methylsulfanylphenyl)cyclopent-2-enol 
• 190966-43-9 2-bromo-3-(4-(methylthio)phenyl)-2-cyclopenten-1-one 

Downstream Products

• 212126-32-4 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one 

Relevant articles and documents

A three-component coupling approach to cyclopentanoids

A new approach to 2,3-disubstituted cyclopentenones has been developed. This approach consists of a two-step protocol involving the cyclization of a Z-vinyl bromide under Barbier type conditions to form a cyclopentenol, which is then oxidatively rearranged to generate the cyclopentenone. The Z-vinyl bromide is in turn derived from a ruthenium catalyzed three-component coupling of an alkyne, an enone, and a HBr equivalent. A range of 2,3-disubstituted cyclopentenones has been generated, including short syntheses of jasmone and dihydrojasmone. Further applicability of this strategy is shown in the total syntheses of tetrahydrodicranenone B, rosaprostol, and a selective COX-2 inhibitor.

Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor

2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence.