55822-06-5

Basic information

• Product Name: 6-Oxabicyclo[3.2.1]oct-3-ene, 4,7,7-trimethyl-, (1R)-
• CAS NO: 55822-06-5
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Mol File: 55822-06-5.mol

Chemical Properties

• CAS DataBase Reference: 6-Oxabicyclo[3.2.1]oct-3-ene, 4,7,7-trimethyl-, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxabicyclo[3.2.1]oct-3-ene, 4,7,7-trimethyl-, (1R)-(55822-06-5)
• EPA Substance Registry System: 6-Oxabicyclo[3.2.1]oct-3-ene, 4,7,7-trimethyl-, (1R)-(55822-06-5)

Safety Data

• Hazardous Substances Data: 55822-06-5(Hazardous Substances Data)

Upstream product

• 76843-92-0 (-)-1-hydroxy-cis-dihydropinol phenylurethane 
• 76843-95-3 (+)-endo-2-hydroxy-1,8-cineol phenylurethane 
• 67-56-1 methanol 
• 14575-92-9 2,3-epoxy-cis-pinane 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 42477-94-1 trans-(S)-(-)-limoneneoxide 
• 79307-11-2 Imidazole-1-carbothioic acid O-((1S,4R,6S)-4-isopropenyl-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl) ester 
• 7632-16-8 (2S,4S)-carveol 
• 7785-70-8 (+)-α-pinene 
• 38235-58-4 trans-sobrerol 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 555-31-7 aluminum isopropoxide 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 

Downstream Products

• 76236-83-4 (+/-)-1-hydroxy-trans-2-tosyloxy-cis-dihydropinol 
• 20178-12-5 1,8-epoxy-p-menthane-2,6-diol 

Relevant articles and documents

A study of some molecularly imprinted polymers as protic catalysts for the isomerisation of α-pinene oxide to trans-carveol

A range of acidic Molecularly Imprinted Polymers (MIPs) were synthesised using the imprint molecule trans-carvyl amine as a transition state analogue for the selective isomerisation of α-pinene oxide to trans-carveol. The amine functionality of the imprint molecule was used to selectively position a sulfonic acid group in the MIP binding pocket utilising 4-styrene sulfonic acid as the functional monomer. Co-polymerisation with varying ratios of styrene and divinylbenzene afforded a range of MIPs which were tested for their ability to effect selective formation of trans-carveol from α-pinene oxide. Although successful imprinting was demonstrated in binding studies, it was shown that solvent effects were dominant in effecting selective formation of trans-carveol. Using DMF as solvent, up to 70% of the products from acid catalysed isomerisation of α-pinene oxide with the polystyrene MIPs were obtained via the necessary para menthyl tertiary carbocation, and industrially important trans-carveol was obtained in 45% yield.

Stereocontrolled Regiospecificity of the Water Loss from trans-Sobrerol Radical Cation upon Electron Ionization

Water loss from trans-sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occuring by a stereocontrolled H-transfer from C(5) position in a rate-determining step process, as proved by 18O and deuterium labelling.Monomethyl ethers behave accordingly.Ionic structures of the water-loss product or products are investigated by metastable ion and collision activation mass-analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to trans-sobrerol in condensed phase, i.e. α-pinane epoxide, cis-sobrerol and pinol.A substantial conversion of cis-sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.

STEREOCHEMISTRY OF DIHYDROPINOL AND 1,8-CINEOL DERIVATIVES. PART VI. SYNTHESIS OF (-)-1,2-PINOL

The method of synthesis of optically pure (-)-1,2-pinol by oxymercuration of (+)-cis-carveol and reduction of a cyclic mercuric compound formed has been discused.A possible mechanism of formation of the side products, tricyclic stereoisomeric compounds, 3,cis-9-dimethyl- and 3,trans-9-dimethyl-2-oxatricyclo3,7>nonane, has been proposed.

REACTION OF CIS-CARVEOL WITH TRIPHENYLPHOSPHINE AND TETRACHLOROMETHANE: A NOTE ON THE MECHANISM OF THE LEE REACTION

The title reaction yielded trans-carvyl chloride 2 and pinol 3.The formation of pinol and the specific rotation of the carvyl chloride are affected by the presence of acid.The implications of these findings on the understanding of the course of he reaction are discussed.Use of an acid scavenger is recommended in application of the PPh3-CCl4 reagent for acid sensitive compounds.A bimolecular, concerted group transfer mechanism (Scheme 2) is suggested for the decomposition of the intermediate alkoxytriphenylphosphonium halide 7.

Radical-induced Ring Opening of Epoxides. A Convenient Alternative to the Wharton Rearrangement

Tri-n-butyltin hydride reduction of an αβ-epoxy-O-thiocarbonylimidazolide derivative of an alcohol leads via oxiran ring-opening to the formation of an allylic alkoxyl radical.By a suitable choice of experimental conditions, this radical can either be quenched by hydrogen-atom transfer from the stannane or allowed to undergo further rearrangement.

STEREOCHEMISTRY OF DIHYDROPINOL AND 1,8-CINEOL DERIVATIVES. PART V. PYROLYSIS OF PHENYLURETHANES FROM THE DIHYDROPINOL AND CINEOL SYSTEMS

Several crystalline phenylurethanes of alcohols from systems of dihydropinol and cineols were prepared.These compounds underwent thermal decomposition (cis-elimination) yielding interesting unsaturated products the structure and mechanism of formation of which were established.