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可见光驱动下由2-羟基查尔酮仿生合成杂合黄酮类化合物。

A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light.

作者信息

Gao Yu-Qi, Hou Yi, Zhu Liming, Chen Guzhou, Xu Dongyang, Zhang Sheng-Yong, He Yupeng, Xie Weiqing

机构信息

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University 22 Xinong Road Yangling 712100 Shaanxi China

College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University Dandong Lu West 1 Fushun 113001 China

出版信息

RSC Adv. 2019 Sep 16;9(50):29005-29009. doi: 10.1039/c9ra07198a. eCollection 2019 Sep 13.

DOI:10.1039/c9ra07198a
PMID:35528404
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9071822/
Abstract

A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is captured by nucleophiles to afford hybrid flavonoids.

摘要

本文描述了一种从2-羟基查尔酮仿生合成杂合黄酮类化合物的方法。在24 W紧凑型荧光灯照射下，2-羟基查尔酮与各种亲核试剂反应，在布朗斯特酸催化下，以良好至优异的产率得到结构多样的杂合黄酮类化合物。此外，使用催化手性磷酸抗衡阴离子导向加成可获得中等对映选择性。基于机理研究，该反应被认为是通过2-羟基查尔酮的串联双键异构化/脱水环化形成一个瞬态黄酮鎓阳离子，该阳离子被亲核试剂捕获以得到杂合黄酮类化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/deaca5b45eb5/c9ra07198a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/ecf5dd6a074c/c9ra07198a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/36a07b3a161d/c9ra07198a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/8212da29e215/c9ra07198a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/93dd71115cb6/c9ra07198a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/3ba6c72b28ed/c9ra07198a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/deaca5b45eb5/c9ra07198a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/ecf5dd6a074c/c9ra07198a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/36a07b3a161d/c9ra07198a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/8212da29e215/c9ra07198a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/93dd71115cb6/c9ra07198a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/3ba6c72b28ed/c9ra07198a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0075/9071822/deaca5b45eb5/c9ra07198a-s5.jpg

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