28582-40-3

Upstream product

• 491-04-3 trans-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 491-04-3 piperitol 
• 4221-98-1 (R)-5-isopropyl-2-methylcyclohexa-1,3-diene 

Downstream Products

• 122305-05-9 trans-3-(4-chloro-2-methyl-2(E)-butenyl)-4-isopropyl-1-methylcyclohex-1-ene 
• 491-04-3 (+)-trans-piperitol 
• 112068-28-7 (3R,4R)-1-methyl-4-(1-methylethyl)-cyclohex-1-en-3-yl acetate 

Relevant academic research and scientific papers

DIASTEREOSELECTIVE SYNTHESIS OF β- AND γ2-MUUROLENE: A CARBOCATIONIC PATHWAY FROM MONO- TO SESQUITERPENES

The Lewis acid catalysed addition of the piperityl chlorides 6 to isoprene yields adduct 7, which undergoes a cis-stereoselective cyclisation to give the diastereoisomeric muurolene monohydrochlorides 8.Treatment with potassium tert-butoxide affords β- an

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.

Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution

cis- and trans-Carvotanacetols and -piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium.The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r. spectroscopy, which permitted assignment of the relative configurations.Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane.The corresponding trimethylstannane is optically inactive.Substitution reactions (SE') with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ-syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.