色酮类化合物的制备及其在有机合成中的应用进展

doi:10.6023/cjoc202403025

摘要/Abstract

色酮是黄酮类化合物的核心骨架, 其衍生物具有不同的应用价值. 同时, 色酮含有的α,β-不饱和酮结构使其能够发生取代、环化、不对称加成等反应, 促进多种功能化的色酮类似物或其他骨架分子的产生. 因此, 除色酮天然产物外, 色酮类化合物的制备及其作为合成子在有机合成中的应用研究同样备受关注. 总结了色酮类化合物的制备方法, 并以反应类型和反应区域作为依据综述了近年来重要色酮类合成子在有机合成中的应用.

关键词: 色酮, 合成子, 官能团化, 加成反应

Chromone is the core backbone of flavonoids and its derivatives have different applications. Meanwhile, the α,β-unsaturated ketone structure contained in chromones enables them to undergo reactions such as substitution, cyclization, and asymmetric addition, which promotes the generation of a variety of functionalized chromone analogues or other backbone molecules. Therefore, in addition to chromone natural products, the preparation of chromones and their use as synthons in organic synthesis applications are also of great interest. The preparation methods of chromones are summarized and the recent applications of important chromone synthons in organic synthesis are reviewed on the basis of reaction types and reaction regions.

Key words: chromones, synthons, functionalization, addition reaction

引用此文

黎忠昊, 曾玉, 曾咏, 徐文锦, 曹西颖, 郭玉婷, 沈晴, 汪朝阳. 色酮类化合物的制备及其在有机合成中的应用进展[J]. 有机化学, 2024, 44(11): 3345-3356.

Zhonghao Li, Yu Zeng, Yong Zeng, Wenjin Xu, Xiying Cao, Yuting Guo, Qing Shen, Zhaoyang Wang. Progresses in the Preparation of Chromone Compounds and Their Applications in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3345-3356.

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图/表 14

图式1. 3-酰基色酮3的合成及其反应机理

Scheme 1. Synthesis and reaction mechanism of 3-acylchromone 3

图式2. 二硫缩烯酮5的内环化及其一锅法反应

Scheme 2. Internal cyclization of ketene dithioacetals 5 and their one-pot reaction

图式3. 由芳醛和卤代烯烃生成色酮

Scheme 3. Synthesis of chromones from aromatic aldehydes and halogenated olefins

图式4. 色酮与三氟乙醇的交叉脱氢偶联

Scheme 4. Cross-dehydrogenative coupling of chromone with polyfluorinated alcohol

图式5. 色酮类化合物的区域选择性硫醚化

Scheme 5. Regioselective sulfenylation of chromones

图式6. 以3-碘色酮为原料合成2,3-二取代色酮衍生物

Scheme 6. Synthesis of 2,3-disubstituted chromone derivatives from 3-iodochromone

图式7. Ru(II)催化下色酮5-位的直接区域选择性硒化

Scheme 7. Direct regioselective selenylation of chromones at the C(5)-position under Ru(II) catalysis

图式8. 钯催化3-碘代色酮和NBE、邻溴苯甲酸的环化反应

Scheme 8. Palladium-catalyzed cyclization of 3-iodochromone with NBE and o-bromobenzoic acid

图式9. 3-碘代色酮与不同组分在钯催化下发生环化

Scheme 9. Palladium-catalyzed cyclization of 3-iodochromones with different components

图式10. 构建多官能化的双螺环色满酮衍生物

Scheme 10. Construction of highly functionalized bispiro[benzofuran-oxindole/benzofuran-chromanone]s

图式11. 路易斯酸催化乙烯基环氧乙烷与3-甲酰色酮的芳构化

Scheme 11. Lewis acid-catalyzed benzannulation of vinyloxiranes with 3-formylchromones

图式12. 不同取代基控制3-取代色酮的开环或稠环化反应

Scheme 12. Different substituents control the ring-opening or fused cyclization of 3-substituted chromones

图式13. 基于色酮合成苯并吡喃腈衍生物及荧光探针

Scheme 13. Synthesis of dicyanomethylene-benzopyran derivatives and fluorescent probes via chromones

图式14. 基于色酮合成荧光探针22

Scheme 14. Synthesis of fluorescent probes 22 via chromones

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