464892-42-0

Basic information

• Product Name: 2-Cyclohexen-1-one, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-, (6S)-
• CAS NO: 464892-42-0
• Molecular Formula: C18H32O2Si
• Molecular Weight: 308.536
• Mol File: 464892-42-0.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-, (6S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-, (6S)-(464892-42-0)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 6-[(1S)-1,5-dimethyl-1-[(trimethylsilyl)oxy]-4-hexenyl]-3-methyl-, (6S)-(464892-42-0)

Safety Data

• Hazardous Substances Data: 464892-42-0(Hazardous Substances Data)

Upstream product

• 465532-29-0 (2S,5R,1'S)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone 
• 464892-38-4 (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol 
• 464892-40-8 (2S,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanone 
• 103615-39-0 (1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol 
• 7786-67-6 isopulegol 
• 673451-17-7 (3R,6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone 

Downstream Products

• 95602-94-1 (6S,1'S)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone 

Relevant articles and documents

Enantiospecific synthesis of (+)-hernandulcin

The sesquiterpene (+)-hernandulcin has been enantiospecifically synthesized starting from (-)-neoisopulegol in seven steps and in 25% overall yield.

A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin

A facile total synthesis of (+)-hernandulcin (1) was accomplished from (-)-isopulegol in 6 steps with 15% overall yield. Epoxidation of (-)-isopulegol with m-chloroperbenzoic acid followed by opening of the epoxide 3a with prenyl Grignard afforded the tertiary alcohol 4a with correct C-6 and C-1′ stereochemistry as a major product. Oxidation of the secondary alcohol in compound 4a to the ketone 5a was accomplished in high yield by using TPAP and N-methylmorpholine N-oxide. Conversion of the ketone 5a to α,β -unsaturated ketone via organoselenium intermediate gave (+)-hernandulcin (1). This method was also successfully applied to the synthesis of (+)-epihernandulcin (2).

Synthesis of (+)-hernandulcin and (+)-epihernandulcin

(+)-Hernandulcin 1, an extremely sweet bisabolane-type sesquiterpene, and (+)-epihernandulcin 2 were synthesized in six steps from (-)-isopulegol with 15 and 11 percent overall yields, respectively.