464892-38-4

Basic information

• Product Name: (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol
• Synonyms: (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol
• CAS NO: 464892-38-4
• Molecular Weight: 240.386
• Mol File: 464892-38-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol(464892-38-4)
• EPA Substance Registry System: (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol(464892-38-4)

Safety Data

• Hazardous Substances Data: 464892-38-4(Hazardous Substances Data)

Upstream product

• 103615-39-0 (1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 7786-67-6 isopulegol 

Downstream Products

• 464892-40-8 (2S,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanone 
• 95602-94-1 (6S,1'S)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone 
• 464892-42-0 (6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-cyclohexenone 
• 465532-29-0 (2S,5R,1'S)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone 
• 673451-17-7 (3R,6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone 

Relevant articles and documents

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).