66965-44-4

Usage

Uses

Used in Fragrance Industry:
(1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one is used as a scent ingredient for its woody, floral, and violet-like odor profile. It is valued in perfumes and other scented products for adding a rich and long-lasting aroma.
Used in Flavoring Industry:
(1)-1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octan-2-one is also utilized as a flavoring agent in certain foods and beverages, enhancing their taste and aroma.

Upstream product

• 873990-46-6 1,3,3-trimethyl-6-oxo-2-oxa-bicyclo[2.2.2]octane-5-carboxylic acid 
• 470-82-6 1,8-Cineole 
• 4112-22-5 chromyl acetate 
• 71208-23-6 1-(2,6-dimethyl-3,4-dihydro-2H-pyran-2-yl)-ethanone 
• 98-55-5 terpineol 
• 18679-48-6 2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) 
• 56031-82-4 2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol 
• 10067-30-8 8,9-diacetoxy-p-menth-1-ene 
• 138-86-3 limonene. 
• 54145-81-2 p-methane-α-1,2-epoxy-8-ol 
• 107553-94-6 1-(2,6-Dimethyl-3,4-dihydro-2H-pyran-2-yl)-2-diazo-1-ethanone 
• 107553-95-7 (1S,2R,5S,7R)-5,7-Dimethyl-6-oxa-tricyclo[3.2.1.0^2,7]octan-8-one 

Downstream Products

• 499-75-2 carvacrol 
• 18679-48-6 (+/-)-β2-hydroxy-1,8-cineole 
• 18679-48-6 2-endo-hydroxy-1,8-cineole ((1R,6R)-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-6-ol) 
• 58701-26-1 6-isopropyl-3-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 867133-54-8 6-(α-bromo-isopropyl)-3-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 72257-53-5 (-)-α2-acetyloxy-1,8-cineole 
• 72257-53-5 (+)-α2-acetyloxy-1,8-cineole 
• 72257-53-5 cis-2-acetoxy-1,8-cineole 
• 72257-53-5 (+)-β2-acetyloxy-1,8-cineole 
• 72257-53-5 (-)-β2-acetyloxy-1,8-cineole 
• 136135-80-3 1,3,3-Trimethyl-5-[1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-meth-(Z)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one 
• 156473-18-6 1,3,3-trimethyl-5-<(4-methylthiophenyl)methylene>-2-oxabicyclo<2.2.2>octan-6-one 
• 136135-81-4 1,3,3-Trimethyl-5-[1-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-meth-(Z)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one 
• 135420-66-5 4-[2-(1,3,3-Trimethyl-6-phenyl-2-oxa-bicyclo[2.2.2]oct-6-yloxy)-ethyl]-morpholine 

Relevant academic research and scientific papers

Syntheses of chiral 1,8-cineole metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole- containing capsules

The chiral metabolites in human urine were investigated after ingestion of a 1,8-cineole (eucalyptol)-containing enterocoated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (-/+)-α2-hydroxy-1,8- cineole, (-/+)-β2-hydroxy-1,8-cineole, (-/+)-9-hydroxy-1,8-cineole, and (-/+)-2-oxo-1,8-cineole were prepared. To achievethis aim, after acetylation of the synthesized racemic 2-and 9-hydroxy-1,8-cineoles, pig liver esterase- or yeast-mediated hydrolysis provided the (-)-alcohols with their antipodal(+)-acetates with enantiomeric excess of 33-100 %. Dess-Martin periodinane oxidation of the alcohol (+)-α2-hydroxy-1,8-cineole, obtained by hydrolysis of the resolved acetate, provided the corresponding (+)-2-oxo-1,8-cineole, meanwhile the oxidation of (-)-α2-hydroxy-1,8-cineole gave (-)-2-oxo-1,8-cineole. Using these standards seven metabolites (+/-)-α2-hydroxy-1,8-cineole, (+/-)-β2-hydroxy-1,8-cineole, (+/-)-α3-hydroxycineole,(+/-)-3-oxo-1, 8-cineole, 4-hydroxy-1,8-cineole, 7-hydroxy-1,8-cineole, and (+/-)-9-hydroxy-1,8-cineole, all liberated from their glucuronides, were identified in urine by GCMS on a chiral stationary phase after consumption of 10 mg of 1,8-cineole. Metabolite screening using 2H3-1,8- cineol as the internal standard revealed (+/-)-α2-hydroxy-1,8-cineole as the predominant metabolite followed by (+/-)-9-hydroxy-1,8-cineole. Furthermore, the results showed that one enantiomer is always formed preferentially.

Regiospecific Functionalization of the Monoterpene Ether 1,3,3-Trimethyl-2-oxabicyclooctane (1,8-Cineole). Synthesis of the Useful Bridged γ-Lactone 1,3-Dimethyl-2-oxabicyclooctan-3-->5-olide

The regiospecific functionalization at C-5 and difuctionalization at C-5/C-8 and C-5/C-10 of the monoterpene 1,3,3-trimethyl-2-oxabicyclooctane (1) is described.Chromyl acetate oxidation of 1 afforded 1,3,3-trimethyl-2-oxabicyclooctan-5-one (6) in 60percent yield along with 28percent of unreacted 1 and minor amounts of exo-1,3,3-trimethyl-2-oxabicyclooctan-5-ol acetate (9), 1,3,3-trimethyl-2-oxabicyclooctane-5,8-dione (13), exo-8-acetoxy-1,3,3-trimethyl-2-oxabicyclooctan-5-one (16), 1,3,3-trimethyl-2-oxabicyclooctane-5,7-dione (14), and orcinol (15).On digestion with oxalic or phthalic acid, ketone 6 was converted into a mixture of piperitenone (20), 3-methyl-2-cyclohexenone (22), acetone, and traces of isopiperitenone (21), while 60percent sulfuric acid at room temperature yielded 20 as the sole reaction product.Oxidation of 6 with chromyl acetate yielded diketone 13, which decomposed into orcinol (15) on digestion with either boiling water or a 2.5percent sodium bicarbonate solution.Sodium borohydride or lithium aluminum hydride reduction of 6 gave stereospecifically exo-1,3,3-trimethyl-2-oxabicyclooctan-5-ol (7) while reduction with sodium-ethanol or aluminum isopropoxide in isopropyl alcohol (equilibrium conditions) yielded a 3:2 mixture of the alcohols 7 and 8, respectively.Treatment of 7 with phosphoryl chloride produced 1,3,3-trimethyl-2-oxatricyclo5,8>octane (25) together with minor amounts of the chlorocineoles 10 and 11.Pyrolysis of the methyl xanthate of 7 yielded 1,3,3-trimethyl-2-oxabicyclooct-5-ene (2).Photolysis of 7 in the presence of mercuric oxide and iodine or iodosylbenzene diacetate and iodine gave the tricyclic diether 29, which was quantitatively converted into the bridged γ-lactone 30 by oxidation with ruthenium tetraoxide.Oxidation of 29 with chromyl acetate yielded a 1:1 mixture of 30 and the formate lactone 31.Lithium aluminum hydride reduction of 30 produced diol 37, which was converted into menthofuran (44) in five steps.

FORMATION OF REACTIVE TRICYCLIC INTERMEDIATES VIA THE INTRAMOLECULAR CYCLOPROPANATION OF DIHYDROPYRANS. SYNTHESIS OF EUCALYPTOL

Tricyclic compound 3 was synthesized via a cyclopropanation reaction promoted by 2.This highly srained compound was found to undergo selective chemical transformations to give oxa-bicyclic ketones.This methodology was applied in a total synthesis of the monoterpene, eucalyptol.

Process for the preparation of 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octan-6-ones

1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octan-6-ones are prepared by first epoxidizing α-terpineol with a peracid and thereafter oxidizing the resulting product with an appropriate oxidizing agent.