10309-65-6

Usage

Uses

Used in Organic Synthesis:
[1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate is used as a key intermediate in the synthesis of complex organic molecules. Its unique structure and functional groups allow for a wide range of chemical reactions, making it a valuable building block for the creation of novel compounds with diverse applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate is used as a starting material for the development of new drugs. Its specific structure and properties can be exploited to design and synthesize bioactive molecules with potential therapeutic applications, such as those targeting various diseases and medical conditions.
Used in Material Science:
[1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate can be utilized in the development of new materials with unique properties. Its molecular structure and functional groups can be tailored to create materials with specific characteristics, such as improved mechanical strength, thermal stability, or chemical resistance, depending on the desired application.

Upstream product

• 936-91-4 3-carene epoxide 
• 57400-93-8 3β-acetoxycaran-4α-ol 
• 22556-08-7 trans-3,4-caranediol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 6380-28-5 carvacryl acetate 
• 4017-83-8 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol 
• 10481-91-1 (+)-4-trans-isopropylene-1-methylbicyclo<3.1.0>hexan-cis-2-ol 

Relevant academic research and scientific papers

THE ALDOL-TYPE CONDENSATION OF LITHIUM, BORON AND TITANIUM ENOLATES OF ISOCARANYL ACETATES WITH BENZALDEHYDE. THE METAL AND CHIRAL AUXILIARY EFFECTS

A new approach to chiral enolates by using a chiral ester (isocaranyl acetates) and a chiral organometallic reagent (boranes and titanates) is reported.The effect of this double enantiodifferentiation and the effects of the isomerism of chiral auxiliary (2- and 4-isocaranyl) and that of the metal (Li, B, Ti) on the enantioselectivity of aldol condensation of 2- and 4-isocaranyl acetates with benzaldehyde are discussed.Lithium and boron enolates of isocaranyl acetates add preferentially to the si-face of benzaldehyde while the addition of analogous titanium enolates occurs preferably on the re-face of the aldehyde.The enolborinate which gives the highest ee value is that obtained by transmetallation reaction of the lithium enolate of (+)-2-isocaranyl acetate with (-)-di-4-isocaranylchloroborane.Obversely the enoltitanate prepared from (-)-4-isocaranyl acetate and the LDA-(+)-di-2-isocaranoxy(chloro)cyclopentadienyl titanate system is that which gives the highest enantiofacial discrimination.The chiral auxiliary effect has been used to plan the synthesis of (+)-4α-acetoxy-3β-trimethylsilyloxy-trans-carane, the titanium enolate of which gives (R)-(+)-β-hydroxy-β-phenylpropionic acid in high enantiomeric excess.

Acid-catalysed Terpenylations of Olivetol in the Synthesis of Cannabinoids

Examination of the toluene-p-sulphonic acid-catalysed reaction of (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide with olivetol shows that, inconsistently with the accepted mechanism, (3R,4R)-(-)-o- and -p-cannabidiols are produced as well as (3R,4R)-(-)-Δ1- and Δ6-tetrahydrocannabinols.Evidence is now presented that, as in Petrzilka's reaction employing chiral p-mentha-2,8-dien-1-ols, the reacting species is the delocalised (4R)-p-mentha-2,8-dien-1-yl cation (9).Similar terpenylation using (1S,3S,4R,6R)-(+)-trans-car-3-ene epoxide shows that besides the reported (-)-Δ6-THC, o- and p-cannabidiols, Δ1-THC and Δ4,8-iso-THC can also be produced.The nature of the products, the chirality, and the characteristics of the reaction implicate again the delocalised cation (9).Its formation via Kropp-type rearrangement is excluded and a pathway leading to (4R)-p-mentha-2,6,8-triene, which on protonation gives (9), is proposed.Protonated on C-8, the triene can be trapped and isolated as (4R)-p-mentha-2,6-dien-8-ol.The latter, made in (+/-)-form from citral, proved to be an excellent terpenylating agent for producing cannabinoids.Terpenylation of olivetol by the pinanes (1S,4S,5S)-(-)-cis-verbenol and (1R,5S,7R)-(+)-cis-chrysanthenol is compared.A major drawback of the latter is partial racemisation which occurs in the verbenone-chrysanthenone isomerisation during its photochemical preparation.Whilst Δ1-THC cannot be directly obtained from verbenol, its tertiary allylic cation permits a much higher yielding terpenylation than the secondary cation from chrysanthenol.