87680-39-5

Basic information

• Product Name: (3S,6R,7S)-1,10-bisaboladien-3-ol
• Synonyms: (3S,6R,7S)-1,10-bisaboladien-3-ol
• CAS NO: 87680-39-5
• Molecular Weight: 222.371
• Mol File: 87680-39-5.mol

Chemical Properties

• CAS DataBase Reference: (3S,6R,7S)-1,10-bisaboladien-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6R,7S)-1,10-bisaboladien-3-ol(87680-39-5)
• EPA Substance Registry System: (3S,6R,7S)-1,10-bisaboladien-3-ol(87680-39-5)

Safety Data

• Hazardous Substances Data: 87680-39-5(Hazardous Substances Data)

Upstream product

• 100572-82-5 1-(1,5-dimethyl-4-hexenyl)-4-methoxy-1,4-cyclohexadiene 
• 112837-26-0 (1R,2R,3S)-2,3-epoxy-3-methylcyclohexyl tosylate 
• 58917-27-4 (R)-sulcatol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 112837-28-2 (1S,5S,6S)-5-iodo-1-methyl-7-oxabicyclo[4.1.0]heptane 
• 112837-25-9 (1R,2R,6S)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-ol 
• 18890-22-7 (R)-3-methylcyclohex-2-en-1-ol 
• 140710-03-8 2-Iodo-3-methyl-2-cyclohexen-1-one 
• 1193-18-6 3-methylcyclohexen-2-one 
• 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 

Downstream Products

• 19888-22-3 β-sesquiphellandrene 
• 38738-45-3 (-)-zingiberene 

Relevant articles and documents

Bisabolane, cyclonerane, and harziane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum cf44-2

Three undescribed bisabolane derivatives, trichaspin, trichaspsides A and B, three undescribed cyclonerane sesquiterpenes, 9-cycloneren-3,7,11-triol, 11-cycloneren-3,7,10-triol, and 7,10-epoxycycloneran-3,11,12-triol, and one undescribed harziane diterpene, 11-hydroxy-9-harzien-3-one, were obtained from the culture of Trichoderma asperellum cf44-2, an endophyte of the marine brown alga Sargassum sp. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and MS data, and their absolute configurations were established by ECD or specific optical rotation data. Trichaspin features an unprecedented ethylated bisabolane skeleton, while trichaspsides A and B represent the first aminoglycosides of bisabolane and norbisabolane sesquiterpenes, respectively. Nine of the compounds were evaluated for inhibition of five marine-derived pathogenic bacteria and toxicity to a marine zooplankton.

Stereoselective anti -S N 2′-Substitutions of Secondary Alkylcopper-Zinc Reagents with Allylic Epoxides: Total Synthesis of (3 S,6 R,7 S)-Zingiberenol

Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti -S N 2′-substitution and retention of configuration of the chiral alkylorganometallic, leading to

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.

Discovery of the aggregation pheromone of the brown marmorated stink bug (Halyomorpha halys) through the creation of stereoisomeric libraries of 1-bisabolen-3-ols

We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.

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.

Efficient Syntheses of β-Sesquiphellandrene and Zingiberenol Employing a Tandem Arylation-Multistep Reduction-Hydrolysis Sequence

The title sesquiterpenes are synthesized in one step from the common intermediate 4-(6-methyl-5-hepten-2-yl)-2-cyclohexen-1-one, which is prepared using a one-pot tandem arylation-multistep reduction-hydrolysis sequence.

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.

A NEW SYNTHON FOR THE REGIOSPECIFIC γ-ALKYLATION OF 2-CYCLOHEXENONES. APPLICATION TO THE SYNTHESIS OF ZINGIBERENOL AND OXYGENATED BICYCLONONANES

The regiospecific γ-alkylation of γ-sulfonylcyclohexenone ketals is described and applied to various synthetic objectives.