通过可见光诱导醌的光重排来预测天然酚类物质

Alexander A. Fadeev, Martin Kotora
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引用次数: 0

摘要

提出了用单色蓝光在溶液中光重排取代苯醌和萘醌的一般方法。在此过程中,醌环转化为对苯二酚,而取代基则在形成的对苯二酚的近端氧上进行去饱和或环化。我们发现无环饱和取代基(如烷基)更倾向于去饱和,而环和无环不饱和取代基(烯丙基、烯丙基、芳基)都有环化的趋势。由于参与取代基的多样性和这种转化的官能团耐受性,我们制备了10种天然酚类化合物,这表明可见光同样可以诱导天然来源的醌形成它们。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Anticipating Natural Phenolics Through Visible Light-Induced Photorearrangement of Quinones

Anticipating Natural Phenolics Through Visible Light-Induced Photorearrangement of Quinones

A general protocol for the photorearrangement of substituted benzo- and naphthoquinones using monochromatic blue light irradiation in solution was developed. During this process, the quinone ring is transformed into the hydroquinone, while the substituent undergoes desaturation or annulation onto the proximal oxygen of the formed hydroquinone. We found that desaturation was preferred for acyclic saturated substituents, such as alkyl groups, and the tendency for annulation was observed for both cyclic and acyclic unsaturated substituents (allyl, alkenyl, aryl). The diversity of the participating substituents and the functional group tolerance of this transformation allowed us to prepare 10 natural phenolic compounds, suggesting that visible light may likewise induce their formation from the respective quinones in natural sources.

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