151951-76-7

Basic information

• Product Name: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone
• Synonyms: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone
• CAS NO: 151951-76-7
• Molecular Weight: 332.507
• Mol File: 151951-76-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone(151951-76-7)
• EPA Substance Registry System: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone(151951-76-7)

Safety Data

• Hazardous Substances Data: 151951-76-7(Hazardous Substances Data)

Upstream product

• 198342-53-9 6-((S)-2,4,6-Triisopropyl-benzenesulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene 
• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 60199-16-8 (1,3,5-triisopropyl)benzenesulfinic acid sodium salt 
• 717-74-8 1,3,5-triisopropyl benzene 

Downstream Products

• 220077-00-9 (2R,3R,R_S)-3-(1,3-dioxolan-2-yl)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-1-cyclopentanone 
• 220076-96-0 (2R,3R,R_S)-3-(hydroxymethyl)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-1-cyclopentanone 
• 220077-22-5 (S)-3-(1,3-dioxolan-2-yl)-1-cyclopentanone 
• 220077-18-9 3-(1,3-dioxolan-2-yl)-2-cyclopentenone 
• 113681-11-1 (S)-3-(hydroxymethyl)-1-cyclopentanone 
• 220076-97-1 (2R,3R,R_S)-3-(1-hydroxy-1-methylethyl)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-1-cyclopentanone 

Relevant articles and documents

Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2-cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the 1H NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the β-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.