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
• Article Data: 8

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

• 76843-95-3 (+)-endo-2-hydroxy-1,8-cineol phenylurethane 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 555-31-7 aluminum isopropoxide 
• 38235-58-4 trans-sobrerol 
• 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 
• 14575-92-9 2,3-epoxy-cis-pinane 
• 67-56-1 methanol 
• 76843-92-0 (-)-1-hydroxy-cis-dihydropinol phenylurethane 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 42477-94-1 trans-(S)-(-)-limoneneoxide 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 

Downstream Products

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

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.

ELECTROOXIDATION OF TERPENES. SYNTHESIS OF PINOL, CARVEOL, AND SOBREROL BY ANODIC OXIDATION OF (-)-α-PINENE

-

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.