环丙烷骨架的构建及其应用研究进展

doi:10.6023/cjoc202507041

摘要/Abstract

环丙烷骨架因其独特的高张力环结构和良好的脂溶性, 在药物化学与燃料化学等多个领域具有重要的理论与应用价值. 系统综述了近二十年来环丙烷骨架结构的构建策略, 涵盖了卡宾/类卡宾与烯烃的环加成反应、叶立德参与的环化反应、金属环丙烷参与的环丙烷化反应、分子内环丙烷化反应, 以及新兴的光催化、电催化和酶催化环丙烷化反应等. 重点分析了相关反应的机理类型、底物适应性与产物立体选择性. 此外, 介绍了环丙烷骨架构建策略在药物研发(如抗病毒剂和神经调节剂等活性分子构建)、天然产物全合成及高能燃料分子设计等领域的重要应用进展. 最后, 展望了环丙烷骨架构建的发展前景, 指出开发新型高效催化剂(如纳米负载型与多孔框架型催化剂)、先进光催化技术及绿色的合成新方法是该领域的重要发展方向.

关键词: 环丙烷, 卡宾, 环丙烷化反应, 合成策略, 药物, 天然产物, 高能燃料

The cyclopropane skeleton holds significant theoretical and practical value in diverse fields, such as medicinal chemistry and fuel chemistry, owing to its highly strained ring structure and favorable lipophilicity. This review systematically summarizes the strategies developed over the past two decades for constructing the cyclopropane framework, including cycloaddition reactions of carbenes and carbenoids with alkenes, ylide-mediated cyclizations, metallocyclopropane-involved cyclopropanations, intramolecular cyclopropanations, as well as emerging photocatalytic, electrocatalytic, and enzymatic cyclopropanation methods. Emphasis is placed on the mechanistic pathways, substrate compatibility, and stereoselectivity of the products. Furthermore, this review highlights the recent advances in the application of cyclopropane construction strategies across various domains, such as drug development (e.g., synthesis of antiviral and neuroregulatory agents), total synthesis of natural products, and the design of high-energy-density fuel molecules. Finally, the future development prospects of cyclopropane synthesis are discussed, pointing to the importance of novel high-efficiency catalysts (e.g., nano-supported and porous framework catalysts), advanced photocatalytic technologies, and greener synthetic methodologies as key research directions.

Key words: cyclopropane, carbine, cyclopropanation reaction, synthetic strategies, medicines, natural products, high-energy fuel

引用此文

郭峻烽, 李春迎, 胡荣贵, 戎豪杰, 李江伟, 杜咏梅, 秦越, 吕剑, 孙道安. 环丙烷骨架的构建及其应用研究进展[J]. 有机化学, 2026, 46(2): 379-398.

Junfeng Guo, Chunying Li, Ronggui Hu, Haojie Rong, Jiangwei Li, Yongmei Du, Yue Qin, Jian* Lü, Dao'an Sun. Advances in the Construction Methods of Cyclopropane Skeleton and Their Applications[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 379-398.

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图/表 45

图式1. 环丙烷对药物药效以及燃料密度和体积热值的影响

Scheme 1. Influence of cyclopropane on pharmacological efficacy as well as fuel density and volumetric calorific value

图式2. 环丙烷化构建策略

Scheme 2. Construction strategy of cyclopropanation

年份	作者	内容
2018	唐功利	总结了天然产物中环丙烷官能团的化学合成与生物合成策略, 主要包括卡宾参与的环丙烷化、分子内S_N2反应、环异构化以及生物合成等策略.
2018	Yury V. Tomilov	主要聚焦于供体-受体环丙烷(Donor-acceptor cyclopropanes, DACs)的合成方法, 包括亲核烯烃与重氮化合物和碘叶立德的反应, 以及亲电烯烃与硫叶立德的反应(Corey-Chaykovsky反应).
2021	Yury V. Tomilov	系统综述了重氮甲烷(CH₂N₂)催化环丙烷化的最新进展, 包括核心催化剂钯基催化剂(如Pd(OAc)₂), 以及安全合成技术和原位生成法, 解决CH₂N₂爆炸性难题; 底物适用性: 单/双取代烯烃、多烯、杂环烯烃均可环丙烷化, 但三取代烯烃需过量CH₂N₂(产率≤50%); 局限性: 不对称环丙烷化效果差(ee<2%).
2019	Marcos G. Suero	总结了2017~2019年光氧化还原催化自由基类卡宾环丙烷化的突破性进展.
2021	王也铭, 王自坤	总结了碘叶立德在有机合成中的研究进展, 其中涉及的环丙烷化反应主要包括金属催化、无金属催化(如PhI(OAc)₂/Bu₄NI体系)、光催化及无催化剂策略.

表1. 环丙烷构建方法的相关综述报道

Table 1. A review of advances in cyclopropane construction methods

图式3. 重氮乙酸乙酯在手性Cu催化剂作用下的烯烃不对称环丙烷化

Scheme 3. Asymmetric cyclopropanation of olefins with ethyl diazoacetate catalyzed by chiral copper catalysts

图式4. 重氮甲烷与不同催化剂催化环丙烷化反应的机制

Scheme 4. Mechanism of cyclopropanation with diazomethane catalyzed by different catalysts

序号	底物	产物	相对反应速率
序号	底物	产物	Pd(OAc)₂	Pd(acac)₂	(Ph₃P)₂PdCl₂
1			1	1	1
2			1.05	1.33	1.12
3			2.25	3.00	3.80
4			2.50	1.68	1.86
5			0.08^a	0.10	—
6			0.02	0.08	0.03
7			≈0.001	≈0.001	<0.002
8			0.18	0.24	0.24

表2. 系列烯烃在Pd(OAc)2、Pd(acac)2和(Ph3P)2PdCl2催化下的相对反应速率

Table 2. Relative reaction rates of a series of olefins catalyzed by Pd(OAc)2, Pd(acac)2, and (Ph3P)2PdCl2

图式5. “管中管”反应器示意图[1]

Scheme 5. Schematic diagram of tube-in-tube reactor[1]

图式6. 氯仿作为二氯卡宾前体对环己烯进行环丙烷化

Scheme 6. Cyclopropanation of cyclohexene using chloroform as a dichlorocarbene precursor

图式7. 萜烯的二氯环丙烷化

Scheme 7. Dichlorocyclopropanation of terpenes

图式8. 偕二卤环丙烷脱卤还原反应

Scheme 8. Reductive dehalogenation of gem-dihalocyclopro- panes

图式9. 文献报道的偕二卤环丙烷脱卤素策略

Scheme 9. Literature-reported strategies for the dehalogenation of gem-dihalocyclopropanes

图式10. Simmons-Smith反应历程

Scheme 10. Mechanism of the Simmons-Smith reaction

图式11. Corey-Chaykovsky环丙烷化反应

Scheme 11. Corey-Chaykovsky cyclopropanation reaction

图式12. 硫叶立德对不饱和碳氢化合物加成反应机制

Scheme 12. Mechanism of sulfur ylide addition to unsaturated hydrocarbons

图式13. 反式-(二氧代)-氮杂双环-[3.1.0]-己烷羧酸盐的合成

Scheme 13. Synthesis of trans-(dioxo)-azabicyclo[3.1.0]-hexa- ne-carboxylate

图式14. 磺鎓盐与醛类及丙二腈在乙醇和离子液体中的三组分反应

Scheme 14. Three-component reaction of sulfonium salts with aldehydes and malononitrile in ethanol and ionic liquids

图式15. 硫叶立德与甲基戊二烯酸酯反应构建环丙烷

Scheme 15. Construction of cyclopropanes via reaction of sulfur ylides with methyl penta-2,4-dienoate

图式16. 碘叶立德合成1,1-环丙烷二酯[43]

Scheme 16. Synthesis of 1,1-cyclopropanediesters using iodonium ylides[43]

图式17. 碘叶立德与缺电子烯烃无催化剂环丙烷化反应

Scheme 17. Catalyst-free cyclopropanation of electron-deficient alkenes using iodonium ylides

图式18. LED蓝光照射下碘叶立德与烯烃的环丙烷化反应

Scheme 18. Photocatalyzed cyclopropanation of alkenes with iodonium ylides under LED blue light irradiation

图式19. 其他叶立德构建环丙烷

Scheme 19. Cyclopropane construction using alternative ylides

图式20. 脂肪族羟酸酯参与的Kulinkovich反应

Scheme 20. Kulinkovich reaction involving aliphatic carboxylate esters

图式21. Kulinkovich反应可能的机理

Scheme 21. Proposed mechanism of the Kulinkovich reaction

图式22. N,N-二烷基酰胺参与的Kulinkovich反应

Scheme 22. Kulinkovich reaction involving N,N-dialkylamides

图式23. 环丙烷合成过程中的活性物种和利用可见光光氧化催化的新自由基方法[13]

Scheme 23. Reactive intermediates in cyclopropane synthesis and a novel radical approach leveraging visible-light photoredox catalysis[13]

图式24. [Cr(Ph2phen)3](BF4)3催化重氮乙酸乙酯对苯乙烯的环丙烷化

Scheme 24. Cyclopropanation of styrene with ethyl diazoacetate catalyzed by [Cr(Ph2phen)3](BF4)3

图式25. 2,2-二溴代丙二酸二乙酯为C1合成子对苯乙烯的环丙烷化

Scheme 25. Cyclopropanation of styrene using diethyl 2,2-dibromomalonate as a C1 synthon

图式26. 电催化环丙烷化

Scheme 26. Electrocatalyzed cyclopropanation

图式27. 铁卟啉催化烯烃环丙烷化和P450酶催化环丙烷化

Scheme 27. Iron porphyrin-catalyzed cyclopropanation of alkenes and P450 enzyme-catalyzed cyclopropanation

图式28. 金属还原法构建环丙烷

Scheme 28. Metal-reductive cyclopropanation

图式29. Wolff-Kishner还原法构建环丙烷

Scheme 29. Construction of cyclopropanes via Wolff-Kishner reduction methodology

图式30. 缩环反应构建环丙烷

Scheme 30. Ring contraction approaches to cyclopropane synthesis

图式31. 丙二酸烷基酯与活化双键构建环丙烷的通用路线

Scheme 31. A general protocol for cyclopropane construction from alkyl malonates and activated alkenes

图式32. 吲哚丙烯醇转化为手性环丙烷中间体

Scheme 32. Conversion of indole acryl alcohols to chiral cyclopropane intermediates

图式33. 利用Simmons-Smith环丙烷化方法转化末端烯烃

Scheme 33. Transformation of terminal alkenes utilizing the Simmons-Smith cyclopropanation protocol

图式34. Ru催化重氮乙酸乙酯对乙烯基吲哚7的不对称环丙烷化

Scheme 34. Ru-catalyzed asymmetric cyclopropanation of vinylindole 7 with ethyl diazoacetate

图式35. 利用Kulinkovich反应合成吡啶基环丙胺12

Scheme 35. Synthesis of pyridylcyclopropylamine 12 utilizing the Kulinkovich reaction

图式36. Tecovirimat的合成线路

Scheme 36. Synthesis route of tecovirimat

图式37. 倍半萜类天然产物Ishwarane的合成

Scheme 37. Total synthesis of the sesquiterpenoid natural product ishwarane

图式38. 倍半萜烯(＋)-Omphadiol的合成

Scheme 38. Total synthesis of the sesquiterpene (＋)-omphadiol

图式39. Pallambins A和B的全合成

Scheme 39. Total synthesis of pallambins A and B

图式40. Ivyane的制备

Scheme 40. Synthesis of ivyane

图式41. 月桂烯环丙烷化

Scheme 41. Cyclopropanation of myrcene

图式42. 蒎烯环丙烷化

Scheme 42. Cyclopropanation of pinene

图式43. 二甲基环戊二烯、5-亚乙基-2-降冰片烯和三环戊二烯的环丙烷化

Scheme 43. Cyclopropanation of dimethylcyclopentadiene, 5-ethylene-2-norbornene, and tricyclopentadiene

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