96633-86-2

Upstream product

• 108-24-7 acetic anhydride 
• 74514-19-5 (2E)-6-chloro-3,7-dimethyl-2,7-octadienyl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 141-12-8 neryl acetate 
• 105831-41-2 (2E)-3,7-dimethyl-2,7-octadien-1-ol acetate 
• 69842-11-1 (2,6,6-trimethylcyclohex-2-en-1-yl)methyl acetate 

Downstream Products

• 91008-65-0 2-Hydroxymethyl-1,3,3-trimethyl-cyclohexanol 

Relevant academic research and scientific papers

CYCLIZATION OF α-TERPENOLS AND THEIR ACETATES BY FLUOROSULFONIC ACID

It has been shown that the superacid cyclization of α-terpenols and their acetates takes place with structural selectivity and chemo- and stereospecificity and leads to cyclic isoprenoids with higher yields than the cyclization of the corresponding β-terpenols and their acetates.

Biomimetic cyclization of small terpenoids promoted by zeolite NaY: Tandem formation of α-ambrinol from geranyl acetone

Zeolite NaY promotes efficiently the biomimetic cyclization of small acyclic terpenes. Geranyl and neryl acetone undergo a novel tandem 1,5-diene cyclization/carbonyl-ene reaction to form the natural product α-ambrinol isolated in >65% yield.

Electrophilic cyclization of α- and β-geranyl acetates by mercury(II) trifluoroacetate

Electrophilic cyclization of β-geranyl acetate promoted by mercury(II) trifluoroacetate leads to mixtures of α- and γ-5αH-cyclogeranyl acetate derivatives and 6α-hydroxy-5αH- and 6α-hydroxy-5βH-cyclogeranyl acetate derivatives mercurated at the C-3 atom. The ratio of the unsaturated and hydroxymercurated products depends on the reaction conditions. α-Geranyl acetate reacts with mercury(II) trifluoroacetate to give a mixture of 6α-hydroxy-5αH- and 6α-hydroxy-5βH-geranyl acetates, mercurated at C-9, with an equatorial mercurated methylene group at C-4. The mercury-containing groups in mercurated cyclogeranyl derivatives can easily be reduced or replaced by an oxygen-containing functional group; this constitutes a convenient route to polyfunctional cyclogeranyl derivatives that are difficult to obtain.

Superacidic low-temperature cyclization of terpenols and their acetates

The superacidic low-temperature cyclization of terpenols and their acetates be fluorosulfonic acid represents a highly efficient chemo- and structurally selective and stereospecific process.Homoallylic alcohols (α-isomers of cycloterpenols) are the products of cyclization of terpenols; the configuration of the hydroxymethyl group in the products is predetermined by the configuration of the allylic double bond in aliphatic or partially cyclized precursors.The cyclization of terpenyl acetates yields monoacetates of fully cyclized diastereomeric primary-tertiary γ-diols.Their stereochemistry also depends on the configuration of the allylic double bond in the starting substrates. - Key words: terpenols; terpenyl acetates; cyclization, fluorosulfonic acid, drimanes, isoagathanes, scarlanes.

CYCLIZATION OF ACYCLIC ISOPRENOIDS. VIII. CYCLIZATION OF GERANIOL, NEROL, AND THEIR ACETATES IN SUPERACIDS

The reaction of geraniol and nerol with HSO3F-SbF5-SO2FCl leads to the formation of an ether identified as 1,4a,8e-trimethyl-7-oxabicyclooctane on the basis of NMR spectral data and chemical transformations.The reactions of geraniol and nerol with

Micellar-Induced Selectivity and Rate Enhancement in the Acid-Catalyzed Cyclization and Rearrangement of Monoterpenes. The Solvolysis of Linalyl and Geranyl Acetates

The monoterpene linalyl acetate (1) undergoes acid-catalyzed solvolysis/cyclization at pH 3 in HCl/citrate buffer to yield three major acyclic alcohols, geranol (2), linalool (3), and nerol (4), and one cyclic alcohol, α-terpineol (5).The acyclic/cyclic alcohol ratio is 2.7 in no sodium dodecyl sulfate (SDS) controls after ca. 3 half-lives, compared to 8.5 when the reaction is carried out in a SDS micelle.No micellar rate effect was observed.The SDS-induced selectivity is explained in terms of the micelle-favoring acyclic conformers of linalyl acetate.In contrast to linalyl acetate, solvolysis of geranyl acetate (6) in the SDS micelle at pH 2 gives little product selectivity but yields a 7-fold rate effect relative to no SDS controls.This rate effect results in very different product distributions after 90percent completion of the reaction.The observed SDS rate effect for geranyl acetate is compatible with a difference in solvolysis mechanism for linalyl and geranyl acetate.