57129-05-2

Upstream product

• 1195-92-2 (4R)-limonene 1,2-epoxide 
• 6909-30-4 (1S,2R,4R)-limonene-1,2-epoxide 
• 174757-62-1 1-((1R,3S,4S)-4-Hydroxy-4-methyl-3-phenylselanyl-cyclohexyl)-ethanone 
• 6090-09-1 methyl-[(1R)-4-methylcyclohex-3-enyl]ketone 
• 5989-27-5 D-limonene 

Downstream Products

• 121383-74-2 (+)-(1S,2R,4R)-endo-1,2-Epoxy-4-ethynyl-1-methylcyclohexane 
• 112837-29-3 (S)-(-)-1-methyl-2-cyclohexen-1-ol 
• 174649-11-7 (1S,4R)-4-acetoxy-1-methyl-2-cyclohexen-1-ol 
• 174649-13-9 Acetic acid (1R,3S,4S)-4-hydroxy-4-methyl-3-phenylselanyl-cyclohexyl ester 

Relevant academic research and scientific papers

Selenoxides as leaving groups: Synthesis of epoxides

β-Hydroxyselenoxides, prepared from substituted cyclohexenes, have been selectively transformed into chiral epoxides by treatment with alkali.

Trichodiene Synthase. Synergistic Inhibition by Inorganic Pyrophosphate and Aza Analogs of the Bisabolyl Cation

A series of aza analogs of the bisabolyl and α-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase.Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone.In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40.The apparent induced inhibition constant αKJ decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog.The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.

Identification and Synthesis of (Z)-(1'S,3'R,4'S)(-)-2-(3',4'-Epoxy-4'-methylcyclohexyl)-6-methylhepta-2,5-diene, the Sex Pheromone of the Southern Green Stinkbug, Nezara viridula (L.)

The sex pheromone of the male green stinkbug, Nezera viridula (L.) has been shown to be a novel epoxybisabolene (Z)-(1'S,3'R,4'S)(-)-2-(3',4'-epoxy-4'-methylcyclohexyl)6-methylhepta-2,5-diene, whose structure has been confirmed by spectroscopic studies and synthesis of the eight possible stereoisomers.