87680-38-4

Basic information

• Product Name: (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol
• Synonyms: (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol
• CAS NO: 87680-38-4
• Molecular Weight: 222.371
• Mol File: 87680-38-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol(87680-38-4)
• EPA Substance Registry System: (1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol(87680-38-4)

Safety Data

• Hazardous Substances Data: 87680-38-4(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 343239-55-4 4-[(1S)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 
• 75-24-1 trimethylaluminum 
• 344903-14-6 8-Benzenesulfonyl-8-(1,5-dimethyl-hex-4-enyl)-1,4-dioxa-spiro[4.5]dec-6-ene 
• 81841-89-6 4,4-(ethylenedioxy)-1-(phenylsulfonyl)cyclohexene 
• 4582-61-0 2-<(tolylsulfonyl)oxy>-6-methyl-5-heptene 
• 100572-82-5 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 1723-80-4 4-(6-methyl-5-hepten-2-yl)-2-cyclohexen-1-one 
• 100572-83-6 4-(1,5-dimethyl-4-hexenyl)-3-cyclohexen-1-one 

Downstream Products

• 1443410-91-0 (3R,6R,7S,10R)-1-bisabolen-3,10,11-triol 
• 1443428-02-1 (3R,6R,7S,10S)-10,11-epoxy-1-bisabolen-3-ol 
• 19888-22-3 β-sesquiphellandrene 
• 38738-45-3 (-)-zingiberene 
• 1454891-14-5 C₁₆H₃₀O₅S 

Relevant articles and documents

Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones

We recently synthesized all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol, including three stink bug pheromones, via a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones. However, yields of trans isomers were low, and scaling reactions using expensive catalysts were cumbersome. Now we describe a new synthesis of bisabolenol stink bug pheromones via (S)- and (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enones prepared by enantioselective Michael additions of methyl vinyl ketone to (S)- and (R)-citronellals and lithium hydroxide monohydrate-catalyzed stereoselective cyclizations of intermediate ketoaldehydes. Addition of methyllithium to these enones provided cis- and trans-1,10-bisaboladien-3-ols, which were separated by chromatography on silica and further converted to 10,11-epoxy-1-bisabolen-3-ols. Thus, we developed more convenient syntheses of pheromones of the rice stink bug, the harlequin bug, and brown marmorated stink bug.

COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS

A composition (useful for attracting Halyomorpha halys) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols : trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl (2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.

Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents

Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.