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通过烯炔醇的光环化/碎片化级联反应实现醛和酮的光化学解笼：环芳构化过程的一种不寻常应用。

Photochemical Uncaging of Aldehydes and Ketones via Photocyclization/Fragmentation Cascades of Enyne Alcohols: An Unusual Application for a Cycloaromatization Process.

作者信息

Campbell Adam, Dos Santos Nikolas R, Alabugin Igor

机构信息

Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA.

出版信息

Molecules. 2023 Jul 28;28(15):5704. doi: 10.3390/molecules28155704.

DOI:10.3390/molecules28155704
PMID:37570675
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10420836/
Abstract

We utilized a cycloaromatization reaction driven by relief of excited state antiaromaticity to photouncage aldehydes and ketones. We developed several synthetic routes towards the synthesis of photocaged carbonyls as allylically substituted 3-(2-(arylethynyl)phenyl)prop-2-en-1-ols. A library of photocaged aryl aldehydes and ketones containing donors and acceptors, as well as several photocaged fragrance aldehydes and the steroid 5α-cholestan- 3 -one, were synthesized and demonstrated photouncaging in good to excellent yields.

摘要

我们利用由激发态反芳香性的缓解驱动的环化芳构化反应对醛和酮进行光解笼。我们开发了几种合成路线来合成作为烯丙基取代的3-(2-(芳基乙炔基)phenyl)丙-2-烯-1-醇的光解笼羰基化合物。合成了一个包含供体和受体的光解笼芳基醛和酮库，以及几种光解笼香料醛和甾体5α-胆甾烷-3-酮，并证明其光解笼反应具有良好至优异的产率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/6a0c78eed1d3/molecules-28-05704-sch009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/2c5cbbefb586/molecules-28-05704-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/274a63246508/molecules-28-05704-sch002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/814bf068e12d/molecules-28-05704-sch006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/e5e577a75c60/molecules-28-05704-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5f59/10420836/6a0c78eed1d3/molecules-28-05704-sch009.jpg

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