非共轭丁烯内酯α-和β-位反应研究进展

doi:10.6023/cjoc202210035

摘要/Abstract

γ-内酯衍生物大多具有抗炎、抗肿瘤和抗癌等生物活性, 发展γ-内酯衍生物的构建方法在有机合成中具有重要价值. 其中, 以非共轭丁烯内酯为起始原料的构建方案呈现出巨大的潜力和无可比拟的优势, 是最直接、高效的方法, 受到化学家的广泛关注, 是近年来有机合成研究热点之一. 综述了非共轭丁烯内酯α-和β-位参与的反应研究进展, 重点概述了各类反应体系的特点, 并对部分反应的机理进行了讨论. 同时, 对该领域未来发展方向进行了展望.

关键词: 非共轭丁烯内酯, α-加成, β-加成, 亲核进攻

Developing the construction methods of γ-lactone derivatives due to their anti-inflammatory, antitumor, anti-cancer and other biological activities has important value in organic synthesis. Among them, the deconjugated butenolides have shown great potential and advantages in the synthesis of γ-lactone derivatives. As the direct and efficient method, it has attracted more attentions of chemists, and is one of the hot topics of organic synthesis in recent years. The α- and β-reactions of deconjugated butenolides are reviewed, in which the characteristics of various reaction systems and the mechanisms of some reactions are discussed. At the same time, the future development is prospected in this field.

Key words: deconjugated butenolides, α-addition, β-addition, nucleophilic attack

引用此文

周林, 杨鸿, 杨川, 赵志刚, 李清寒. 非共轭丁烯内酯α-和β-位反应研究进展[J]. 有机化学, 2023, 43(7): 2407-2424.

Lin Zhou, Hong Yang, Chuan Yang, Zhigang Zhao, Qinghan Li. Advances on the α- and β-Reactions of Deconjugated Butenolides[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2407-2424.

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图/表 23

图1. 含γ-内酯结构的药理活性分子

Figure 1. Pharmacologically active molecules containing γ- lactone

图2. 2-硅氧基呋喃、共轭丁烯内酯和非共轭丁烯内酯的反应活性比较

Figure 2. Reactivity comparison between 2-silyloxy furans, conjugated butenolides and deconjugated butenolides

图式1. 非共轭丁烯内酯的常见反应特性

Scheme 1. Commonly encountered reactivities of deconjugated butenolides

图式2. 非共轭丁烯内酯的合成方法

Scheme 2. Synthetic methods of deconjugated butenolides

图式3. 非共轭丁烯内酯与脂肪醛的Aldol缩合

Scheme 3. Aldol condensation of deconjugated butenolides with alkyl aldehydes

图式4. 非共轭丁烯内酯与查尔酮的Michael加成

Scheme 4. Michael addition of deconjugated butenolides with chalcones

图式5. α-当归内酯与β-卤代-α-酮酸酯的非对映选择性α-Aldol缩合

Scheme 5. Diastereoselective α-Aldol condensation of α-angelica lactone with β-halo-α-ketoesters

图式6. α-当归内酯与硝基烯的不对称α,γ-双Michael加成

Scheme 6. Asymmetric α,γ-double Michael additions of α-angelica lactone with nitroolefines

图式7. 非共轭丁烯内酯与环状N-磺酰亚胺的α-加成串联消除反应

Scheme 7. α-Addition cascade elimination of deconjugated butenolides with cyclic N-sulfonylated imines

图式8. 非共轭丁烯内酯与α-酮酸酯的直接α-加成串联异构化

Scheme 8. Direct α-addition cascade isomerization of deconjugated butenolides with α-ketoesters

图式9. α-当归内酯与三氟甲基苯乙酮的直接α-加成串联异构化

Scheme 9. Direct α-addition cascade isomerization of α-ange- lica lactone with trifluoromethylacetophenone

图式10. 非共轭丁烯内酯与o-QMs的直接α-加成串联酯交换反应

Scheme 10. Direct α-addition cascade transesterification of deconjugated butenolides with o-QMs

图式11. 非共轭丁烯内酯与乙烯基取代环状氨基甲酸酯的直接α-加成串联氨解反应

Scheme 11. Direct α-addition cascade aminolysis of deconjugated butenolides with cyclic vinyl carbamates

图式12. 非共轭丁烯内酯与环状炔丙基氨基甲酸酯的不对称α-取代串联氨解反应

Scheme 12. α-Substitution cascade aminolysis of deconjugated butenolides with cyclic propargylic carbamates

图式13. 非共轭丁烯内酯的直接α-双硫代反应

Scheme 13. Direct α-bis-sulfenylation of deconjugated butenolides

图式14. α-甲基-γ-苯基非共轭丁烯内酯的直接α-硫代反应

Scheme 14. Direct α-sulfenylation of α-methyl-γ-phenyl deconjugated butenolides

图式15. α-甲基-γ-苯基非共轭丁烯内酯的催化不对称α-硫代反应

Scheme 15. Catalytic asymmetric α-sulfenylation of α-methyl- γ-phenyl deconjugated butenolides

图式16. 非共轭丁烯内酯与对亚甲基化醌的β-1,6共轭加成

Scheme 16. Direct β-1,6-conjugate addition of deconjugated butenolides with p-quinone methides

图式17. 非共轭丁烯内酯与脂肪醛的β-Aldol缩合串联酯交换反应

Scheme 17. β-Aldol condensation cascade transesterification of deconjugated butenolides with alkyl aldehydes

图式18. α-当归内酯参与的直接β-加成串联分子内氨解环化

Scheme 18. Direct β-addition cascade intramolecular ammonolysis cyclization of α-angelicalactone

图式19. α-当归内酯与甘氨酸酯的有氧氧化偶联串联氨解

Scheme 19. Aerobic oxidative cross-coupling cascade aminolysis of α-angelicalactone with glycine esters

图式20. α-当归内酯参与的β-加成串联氨解环化的可能机理

Scheme 20. Proposed mechanism of the β-addition cascade ammonolysis cyclization of α-angelicalactone

图式21. 非共轭丁烯内酯与亚硝基化合物的β,γ-双官能化反应

Scheme 21. β,γ-Bifunctional reaction of deconjugated butenolides with nitrosocarbonyl compounds

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