159849-08-8

Basic information

• Product Name: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
• Synonyms: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
• CAS NO: 159849-08-8
• Molecular Weight: 204.356
• Mol File: 159849-08-8.mol

Chemical Properties

• CAS DataBase Reference: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(159849-08-8)
• EPA Substance Registry System: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene(159849-08-8)

Safety Data

• Hazardous Substances Data: 159849-08-8(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 196193-23-4 4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 
• 2385-77-5 (R)-Citronellal 
• 72346-44-2 (3R,6S,7R)-1,10-bisaboladien-3-ol 
• 72346-45-3 (3S,6S,7R)-1,10-bisaboladien-3-ol 
• 75-16-1 methylmagnesium bromide 
• 131308-24-2 (2RS,3R)-3,7-Dimethyl-2-(3-oxobutyl)oct-6-enal 

Downstream Products

• 862260-18-2 (24R)-epi-biyouyanagin A 
• 287-23-0 cyclobutane 
• 1046160-37-5 C₃₁H₃₇FO₄ 
• 1046160-38-6 C₃₂H₄₀O₅ 
• 1046160-39-7 C₃₁H₄₀O₄ 
• 1242140-85-7 biyouyanagin B 
• 1242140-80-2 C₃₁H₃₈O₄ 

Relevant articles and documents

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.

Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof

Isolated from Hypericum species H. Chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic analysis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysacc

Total synthesis and revised structure of biyouyanagin A

(Chemical Equation Presented) It all adds up: A 12-step total synthesis of biyouyanagin A, an inhibitor of HIV replication, has revealed its structure, rendered it available for biological investigations, and allows the synthesis of analogues. The convergent synthesis involves two cascade sequences and a remarkably selective [2+2] cycloaddition reaction to forge the cyclobutane ring of the target molecule in the ultimate step.