690233-31-9

Usage

Uses

Used in Organic Chemistry:
2,4,6-Cycloheptatrien-1-one, 3-hydroxy-2-methoxy(9CI) is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the development of new organic molecules.
Used in Pharmaceutical Industry:
2,4,6-Cycloheptatrien-1-one, 3-hydroxy-2-methoxy(9CI) is used as a potential pharmaceutical candidate for the development of new drugs. Its unique structure and properties may contribute to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Drug Synthesis:
2,4,6-Cycloheptatrien-1-one, 3-hydroxy-2-methoxy(9CI) is used as a starting material in the synthesis of various pharmaceutical compounds. Its presence in the molecular structure can influence the pharmacological properties of the final drug product, potentially leading to the development of more effective and safer medications.

Upstream product

• 79763-03-4 2,2,4-endo-trichloro-8-oxabicyclo<3.2.1>oct-6-en-3-one 

Relevant academic research and scientific papers

A novel synthesis of 2-alkoxy-3-hydroxytropones and 2,7-dihydroxytropones from dialkoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones

Trichloro-substituted 8-oxabicyclo[3.2.1]oct-6-en-3-ones 6 and 7 are solvolysed by methanolic sodium methoxide to form the bicyclo[3.2.1] α,α-dimethoxy ketones 13 and 14, with preservation of one chloro substituent. In the case of 6a, prolonged reaction time with an excess of methanolic sodium methoxide provides a trimethoxy-substituted oxanorbornene aldehyde 19 through ring contraction. Treatment of the mixture of 13 and 14 with zinc and aqueous acetic acid affords dechlorinated α-oxo acetals 15 and 16. Starting with the [4+3] cycloadducts derived from 2-methylfuran and tetrachloroacetones (6b and 7b), the same procedure, but with use of ethanol or trifluoroethanol, results in the corresponding ethoxy- and trifluoroethoxy acetals. These compounds can be converted into the oxabicyclic compounds 15, which undergo cleavage of the ether bridge on heating with KOH in methanol, thus providing 2-alkoxy-3-hydroxytropones 20, which can be dealkylated to give the 2,7-dihydroxytropones (7-hydroxytropolones) 29. The lithium enolate generated from the α-oxo acetal 15a can be exo-alkylated with methyl iodide. Michael addition with 2-nitro-1-butene followed by a Nef reaction furnishes the bicyclic dioxo acetal 5. Treatment of 5 with basic methanol results in an epoxyazulenone derivative 26, and a hydroxytropone 20f, which is in equilibrium with the cyclic hemiacetal form 28. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.