165904-79-0

Basic information

• Product Name: (R)-phenyl γ-cyclothiogeranate
• CAS NO: 165904-79-0
• Molecular Weight: 260.4
• Mol File: 165904-79-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-phenyl γ-cyclothiogeranate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-phenyl γ-cyclothiogeranate(165904-79-0)
• EPA Substance Registry System: (R)-phenyl γ-cyclothiogeranate(165904-79-0)

Safety Data

• Hazardous Substances Data: 165904-79-0(Hazardous Substances Data)

Upstream product

• 113793-67-2 phenyl β-cyclothiogeranate 

Downstream Products

• 166022-20-4 (R)-γ-cyclogeranic acid 
• 166022-33-9 ((R)-(-)-2,2-dimethyl-6-methylene-1-cyclohexyl)methanol 
• 166022-31-7 1-((R)-2,2-Dimethyl-6-methylene-cyclohexyl)-but-3-en-1-one 

Relevant articles and documents

Syntheses of the enantiomers of γ-cyclogeranic acid, γ-cyclocitral, and γ-damascone: Enantioselective protonation of enolates

(R)- and (S)-γ-cyclogeranic acid ((R)- and (S)-9, resp.) were obtained by resolution of the racemate, and their absolute configurations determined by chemical correlation. The γ-acids (R)- and (S)-9 were converted into (R)- and (S)-methyl γ-cyclogeranate ((R)- and (S)-6, resp.), and (R)- and (S)-γ-damascone ((R)- and (S)-5, resp.). A more direct entry to (R)- and (S)-9 consisted in the enantioselective protonation of a thiol ester enolate with (-)- or (+)-N-isopropylephedrine ((-)- or (+)-20) and subsequent hydrolysis of the (R)- and (S)-S-phenyl γ-thiocyclogeranate ((R)- and (S)-24, resp.; 97% ee). The esters (R)- and (S)-24 were also used as precursors of (R)- and (S)-γ-damascone ((R)- and (S)-5, resp.). Alternatively, (S)-5 (75% ee) was obtained by enantioselective protonation of ketone enolate 29 with (-)-N- isopropylephedrine ((-)-20). Organoleptic evaluation demonstrated that the (S)-enantiomers of methyl γ-cyclogeranate and γ-damascone are markedly superior to their (R)-enantiomers.