手性甲基脂肪烃类昆虫信息素的合成研究进展

doi:10.6023/cjoc202103007

摘要/Abstract

手性甲基脂肪烃类昆虫信息素包括单手性甲基、双手性甲基和多手性甲基脂肪烃类昆虫信息素, 在棘翅夜蛾、南部云杉天牛、桃潜叶蛾等多种农林害虫的绿色防控领域具有极具发展的前景. 按手性甲基的构建方法, 分类阐述了单手性甲基昆虫信息素的合成方法; 根据手性甲基片段的连接策略对双手性甲基与多手性甲基脂肪烃类昆虫信息素的合成方法进行了详细介绍; 并对各种合成方法的优势与不足进行简单讨论, 以及对手性甲基脂肪烃类昆虫信息素的合成研究进行了展望.

关键词: 手性甲基, 昆虫信息素, 不对称合成, 连接策略, 进展

The chiral methyl-branched aliphatic hydrocarbon insect pheromones including single, double and multichiral methyl-branched insect pheromones are the most promising green control ofScoliopteryx libatrix,Monochamus titillator,Lyonetia clerkellaand other many pests. The syntheses of single chiral methyl-branched pheromones are reviewed according to the methods of constructing chiral methyl, whereas the preparation of double chiral methyl-branched and multichiral methyl-branched ones are illustrated on the basis of the linking strategies of the key fragments. Moreover, the advantages and disadvantages of the synthetic approaches are discussed, as well as the prospects for the synthesis of chiral methyl-branched aliphatic hydrocarbon insect pheromones.

Key words: chiral methyl, insect pheromone, asymmetric synthesis, linking strategies, progress

引用此文

袁谷城, 边庆花, 王敏, 钟江春. 手性甲基脂肪烃类昆虫信息素的合成研究进展[J]. 有机化学, 2021, 41(7): 2571-2586.

Gucheng Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2571-2586.

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图/表 23

图1. 单手性甲基脂肪烃类昆虫信息素

Figure 1. Single chiral methyl-branched hydrocarbon insect pheromones

图式1. 昆虫信息素1的合成

Scheme 1. Synthesis of insect pheromone 1

图式2. 昆虫信息素2的合成

Scheme 2. Synthesis of insect pheromone 2

图式3. 昆虫信息素3的合成

Scheme 3. Synthesis of insect pheromone 3

图式4. 不对称催化法合成昆虫信息素4

Scheme 4. Asymmetric catalytic synthesis of insect pheromone 4

图式5. 化学拆分法合成昆虫信息素4

Scheme 5. Synthesis of insect pheromone 4 via chemical resolution

图式6. 昆虫信息素5的合成

Scheme 6. Synthesis of insect pheromone 5

图式7. 昆虫信息素6的合成

Scheme 7. Synthesis of insect pheromone 6

图2. 双手性甲基脂肪烃类昆虫信息素

Figure 2. Double chiral methyl-branched hydrocarbon insect pheromones

图式8. Wittig偶联法合成昆虫信息素46

Scheme 8. Synthesis of insect pheromone 46 via Wittig coupling

图式9. 昆虫信息素47的合成

Scheme 9. Synthesis of insect pheromone 47

图式10. 昆虫信息素49的合成

Scheme 10. Synthesis of insect pheromone 49

图式11. 砜烷基化法合成昆虫信息素48

Scheme 11. Synthesis of insect pheromone 48 via the alkylation of sulfone

图式12. 昆虫信息素50的合成

Scheme 12. Synthesis of insect pheromone 50

图式13. 昆虫信息素51的合成

Scheme 13. Synthesis of insect pheromone 51

图式14. 有机锂与醛加成法合成昆虫信息素46

Scheme 14. Synthesis of insect pheromone 46 via the addition of organic lithium to aldehyde

图式15. TosMIC烷基化法合成昆虫信息素47

Scheme 15. Synthesis of insect pheromone 47 via the alkylation of TosMIC

图式16. 环烯酮不对称加成法合成昆虫信息素48

Scheme 16. Synthesis of insect pheromone 48 via the asymmetric addition of cyclic enone

图式17. 手性源法合成昆虫信息素46

Scheme 17. Synthesis of insect pheromone 46 from chiral source

图3. 多手性甲基脂肪烃类昆虫信息素

Figure 3. Poly chiral methyl-branched hydrocarbon insect pheromones

图式18. 昆虫信息素143的合成

Scheme 18. Synthesis of insect pheromone 143

图式19. Wittig反应法合成昆虫信息素144

Scheme 19. Synthesis of insect pheromone 144 via Wittig reaction

图式20. 格氏试剂取代反应法合成昆虫信息素144

Scheme 20. Synthesis of insect pheromone 144 via the substitution of Grignard reagent

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