56031-79-9

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General Description

1,5-dimethyl-9-oxabicyclo[6.1.0]non-4-ene is an organic compound that belongs to the class of bicyclic compounds. It is also known as tropolone and is commonly used as a building block in organic synthesis. This chemical compound contains a bicyclic ring structure with a five-membered oxygen-containing ring fused to a six-membered ring. Tropolone has been studied for its various biological activities and has been found to possess antimicrobial, antiviral, and anti-inflammatory properties. It is also used as a chelating agent in the coordination chemistry of transition metal ions. Tropolone is considered to be a versatile molecule with potential applications in the pharmaceutical and agricultural industries. However, its synthetic pathway and chemical properties need to be further explored and optimized for its efficient and sustainable production and utilization.

InChI:InChI=1/C10H16O/c1-8-4-3-7-10(2)9(11-10)6-5-8/h4,9H,3,5-7H2,1-2H3/b8-4-

Upstream product

• 73022-52-3 1,5-dimethyl-1,5-cyclooctadiene 

Relevant academic research and scientific papers

Substituent-Directed Oxidation: The Syn Stereochemistry of Addition of High-Valent Oxochromium Reagents to Alkenes

The transannular oxidative cyclization of cycloalkenols is a useful synthetic method for the intramolecular syn alkoxyhydroxylation of an alkene, a transformation for which there is presently no alternative procedure.Under the influence of certain high-valent chromium reagents, a cycloalkene substrate that also bears a suitably disposed tertiary hydroxyl ligand first binds the oxidant and then undergoes selective oxidative attack of the tethered oxidant on the alkene.The substrate 1-methylcyclooct-4-en-1-ol (1) is oxidized in a regiospecific fashion to 1-methyl-9-oxabicyclononan-5-one (2) by pyridinium chlorochromate (PCC), while none of the regioisomeric 1-methyl-9-oxabicyclononan-4-one is produced.A regio- and stereospecific oxidative cyclization of 1,5-dimethylcyclooct-4-en-1-ol (3) occurs on treatment with PCC, to yield the exo alcohol isomer of 2,6-dimethyl-9-oxabicyclononan-2-ol (4a), the result of syn oxidative addition of the hydroxyl-bound oxochromium moiety across the carbon-carbon double bond.The endo alcohol isomer of 2,6-dimethyl-9-oxabicyclononan-2-ol (4b) is prepared for comparison by stereospecific addition of tetramethylzirconium to 2.Standard MCPBA epoxidation of 3 gives rise to a mixture of the cis epoxide, endo-1,5-dimethyl-9-oxabicyclononan-5-ol (5), and the product of rearrangement of the trans epoxide, endo-1,5-dimethyl-9-oxabicyclononan-2-ol (6).The cis epoxide 5 on further treatment with PCC is not converted to exo alcohol (4a), indicating that an epoxide intermediate is not involved in the highly specific transannular oxidative cyclization of 3 with chromate.