72311-07-0

Basic information

• Product Name: (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone
• Synonyms: (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone
• CAS NO: 72311-07-0
• Molecular Weight: 206.328
• Mol File: 72311-07-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone(72311-07-0)
• EPA Substance Registry System: (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enone(72311-07-0)

Safety Data

• Hazardous Substances Data: 72311-07-0(Hazardous Substances Data)

Upstream product

• 1046160-17-1 (2S,3R)-3,7-dimethyl-2-(3-oxobutyl)oct-6-enal 
• 2385-77-5 (R)-Citronellal 

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.

Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification

Cedrane sesquiterpenes possess common tricyclo[5.3.1.01,5]undecane core structure. The varied oxa-five-membered ring decorating their core structure to form 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework, containing six consecutive chiral centers (including two all-carbon quaternary centers and one oxygenated quaternary carbon center), has proven to be a synthetic challenge and a biosynthetic mystery to date. Herein, we reported a distinct and biomimetic strategy to these sesquiterpenes resulting in the concise asymmetric total syntheses of three cedrane sesquiterpenes from simple commercially available building blocks. Key feature is exploitation of a cascade oxidative dearomatization-induced [5+2] cycloaddition/etherification to highly stereocontrolled construct 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework with five contiguous chiral centers in one step. In addition, a metal-free I2-catalyzed and DMSO-mediated oxidative dehydroaromatization was applied to prepare curcuphenol and its derivatives from the highly functionalized cyclohexenones with minimal manipulations.

Absolute Configurations of Stink Bug- And Plant-Produced Sesquipiperitols via Synthesis of All Stereoisomers

Sesquipiperitol is a sesquiterpene alcohol, some stereoisomers of which were found in several plant species. The biological role of these compounds in plants and their absolute configurations have not been reported. Recently, we found that 1S,6S,7R stereoisomer of sesquipiperitol was a key precursor in the biosynthesis of the harlequin bug, Murgantia histrionica, pheromone, which consists of two stereoisomeric zingiberenol oxides. In addition, the Tibraca limbativentris stink bug was shown to produce two sesquipiperitol stereoisomers as minor components in their male-produced sex pheromone, the main constituents of which were zingiberenols. To determine absolute configurations of plant- and stink-bug-produced sesquipiperitols, we undertook syntheses of all stereoisomers of this sesquiterpene alcohol. The syntheses were based on 1,10-bisaboladien-3-ols (aka zingiberenols) with known configurations at C-6 and C-7, the oxidation of which provided sesquipiperitone precursors with retention of configurations of these stereogenic centers. The foremost challenge of the synthetic endeavor was the assignment of absolute configurations of secondary carbinol centers, which was resolved by NMR analyses of corresponding Mosher's esters. Thus, the availability of all eight diastereomers allowed us to assign sesquipiperitols from Fitzroya cupressoides and Argyranthemum adauctum spp. jacobaeifolium plants 1S,6S,7R (16) and 1R,6R,7S (14) configurations, respectively. A chiral-phase gas-chromatographic method was developed to determine 1S,6S,7R and 1R,6S,7R (15) configurations of T. limbativentris sesquipiperitol pheromone components.

Total synthesis and structural revision of biyouyanagin B

Figure Presented An intriguing chase of the newly reported biyouyanagin B leads to its total synthesis and structural revision from 1' to 1.

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