基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展

doi:10.6023/cjoc202502005

有机化学 ›› 2025, Vol. 45 ›› Issue (6): 1920-1945.DOI: 10.6023/cjoc202502005 上一篇下一篇

综述与进展

基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展

魏泽齐^†, 孙鑫浩^†, 黎思瑞, 宋汪泽^*()

大连理工大学化学学院辽宁大连 116024

收稿日期:2025-02-04 修回日期:2025-03-24 发布日期:2025-04-24
通讯作者: 宋汪泽
作者简介:
^†共同第一作者.
基金资助:
中央高校基本科研业务费(DUT24YG125); 中央高校基本科研业务费(DUT24ZD114); 中央高校基本科研业务费(2023JH2/101700293); 国家大学生创新创业训练计划(20251014110007)

Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification

Zeqi Wei^†, Xinhao Sun^†, Sirui Li, Wangze Song^*()

School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024

Received:2025-02-04 Revised:2025-03-24 Published:2025-04-24
Contact: Wangze Song
About author:
^†The authors contributed equally to this work.
Supported by:
Fundamental Research Funds for the Central Universities(DUT24YG125); Fundamental Research Funds for the Central Universities(DUT24ZD114); Fundamental Research Funds for the Central Universities(2023JH2/101700293); National College Students’ Innovation and Entrepreneurship Training Program(20251014110007)

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摘要/Abstract

二氢吡喃类化合物是一种常见于天然产物中的含氧杂环类化合物, 具有广泛的生物活性, 同时也是糖类化合物及一些天然产物的重要合成前体. 因此, 研究这类化合物及其衍生物的合成方法具有重要意义. 根据生成二氢吡喃结构的不同, 主要综述了氧基、碳基和氮基二氢吡喃类衍生物的合成研究进展, 并探讨了相关反应的机理和应用范围.

关键词: 二氢吡喃, 氧基二氢吡喃类衍生物, 碳基二氢吡喃类衍生物, 氮基二氢吡喃类衍生物

Dihydropyran compounds are one of oxygen-containing heterocyclic compounds widely existing in natural products and have a wide range of biological activities. They are also important synthetic precursors of carbohydrate compounds and some natural products. Therefore, it is of great significance to study the synthesis of these compounds and their derivatives. According to the different dihydropyran products, this review mainly focuses on the research progress in the synthesis of dihydropyran derivatives substituted by oxygen-, carbon-and nitrogen-based groups, and discusses the related mechanism and application range of related reactions.

Key words: dihydropyrans, oxygen-based dihydropyran derivatives, carbon-based dihydropyran derivatives, nitrogen-based dihydropyran derivatives

引用此文

魏泽齐, 孙鑫浩, 黎思瑞, 宋汪泽. 基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展[J]. 有机化学, 2025, 45(6): 1920-1945.

Zeqi Wei, Xinhao Sun, Sirui Li, Wangze Song. Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1920-1945.

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图/表 76

图1. 二氢吡喃的结构及具有生物活性的二氢吡喃类衍生物

Figure 1. Structure of dihydropyrans and bioactive dihydropyran derivatives

图式1. 两种主要合成二氢吡喃类衍生物方法

Scheme 1. Two main methods for the synthesis of dihydropyran derivatives

图式2. 铼催化合成氧苷糖类化合物

Scheme 2. Re-catalyzed the synthesis of oxyglycoside compounds

图式3. 钯催化立体选择性合成二氢吡喃类衍生物

Scheme 3. Pd-catalyzed stereoselective synthesis of dihydropyran derivatives

图式4. 钯催化立体选择性合成α-O-苷糖

Scheme 4. Pd-catalyzed stereoselective synthesis of α-O-glyco-sides

图式5. 金催化合成二氢吡喃类氧基衍生物

Scheme 5. Au-catalyzed synthesis of dihydropyranyl oxygen derivatives

图式6. 钯催化通过二氢吡喃立体选择性合成3-脱氧糖

Scheme 6. Pd-catalyzed stereoselective synthesis of 3-deoxy-glycosides from dihydropyrans

图式7. 钯催化3-O-酰化糖烯的立体选择性α-O-糖基化反应

Scheme 7. Pd-catalyzed α‑stereoselective O‑glycosylation of 3-O‑acylated glycals

图式8. Pd(0)和Pd(Ⅱ)催化立体选择性O-糖基化反应

Scheme 8. Pd(0) and Pd(Ⅱ)-catalyzed stereoselective O-glycosylation

图式9. 金催化立体选择性合成3-脱氧糖

Scheme 9. Au-catalyzed stereoselective synthesis of 3-deoxyglycosides

图式10. 温度和布朗斯特酸调控硅基保护鼠李糖类化合物的转化

Scheme 10. Temperature and Brønsted acid-controlled the trans-formation of silyl protected rhamnals

图式11. 钯催化空气氧化糖烯与芳基硼酸的立体选择性O-糖基化反应

Scheme 11. Pd-catalyzed stereoselective O-glycosylation of glycals with arylboronic acids using air as the oxidant

图式12. 钯催化糖烯与醇的立体发散性O-糖基化反应

Scheme 12. Pd-catalyzed stereodivergent O-glycosylation of glycals and alcohols

图式13. 钯催化合成氧基3,4-二氢吡喃酮类衍生物

Scheme 13. Pd-catalyzed the synthesis of 3,4-dihydropyranoneoxy derivatives

图式14. 以Achmatowicz重排产物为原料合成3,4-二氢吡喃酮类衍生物

Scheme 14. Synthesis of 3,4-dihydropyranone derivatives from the products of Achmatowicz rearrangement

图式15. 钯催化合成寡聚二氢吡喃酮衍生物

Scheme 15. Pd-catalyzed synthesis of oligopyranone derivatives

图式16. 路易斯酸催化糖苷化反应

Scheme 16. Lewis acid-catalyzed the glycosidation

图式17. 钯催化D-酪氨酸和二氢吡喃酮的反应

Scheme 17. Pd-catalyzed reaction of D-tyrosine and dihydropyranones

图式18. 以山奈酚为原料合成二氢吡喃酮类衍生物

Scheme 18. Synthesis of dihydropyranone derivatives derived from perbenzylated kaempferol

图式19. 3,4-二氢吡喃类衍生物的化学选择性糖基化

Scheme 19. Chemoselective glycosylations using 3,4-dihydropyranone derivatives

图式20. 钯催化的烯丙酯的动力学拆分

Scheme 20. Pd-ctalyzed kinetic resolution of allylic esters

图式21. 碱促进合成双环缩醛化物

Scheme 21. Base-promoted synthesis of bicyclic acetal compound

图式22. 二氢吡喃酮的动态动力学选择性酰化反应

Scheme 22. DKEAT of dihydropyranones

图式23. DKDA法高立体选择性合成氧基二氢吡喃酮衍生物

Scheme 23. High stereoselective synthesis of oxydihydropyranone derivatives by DKDA method

图式24. NHC催化二氢吡喃酮的动态动力学选择性酰化反应

Scheme 24. NHC-catalyzed dynamic kinetic stereoselective acylation of dihydropyranones

图式25. 金或银催化合成二氢吡喃酮类氧基衍生物

Scheme 25. Au or Ag-catalyzed the synthesis of dihydropyranoneoxy derivatives

图式26. 铱催化的氧化还原异构化反应

Scheme 26. Ir-catalyzed redox isomerization

图式27. 酶催化的氧化还原异构化反应

Scheme 27. Enzyme-catalyzed redox isomerization

图式28. 路易斯酸催化以烯醇硅烷为供体的C-糖基化反应

Scheme 28. Lewis aicd-catalyzed C-glycosylation with enol-silane as donor

图式29. 钯催化过糖烯与芳基硼酸的立体选择性C-糖苷化反应

Scheme 29. Pd-catalyzed stereoselective C-glycosidation of glycals with arylboronic acids

图式30. 有机锌试剂与2,3-二氢吡喃的立体选择性加成反应

Scheme 30. Stereoselective addition reaction between organo-zinc reagents and 2,3-dihydropyrans

图式31. 路易斯酸催化的炔基三氟硼酸钾与D-葡萄糖的亲核加成反应

Scheme 31. Lewis acid-catalyzed nucleophilic addition of acetylenyl potassium trifluoroborate with D-glucose

图式32. 氧化剂控制的二氢吡喃与芳基硼酸的Heck-型C-糖基化反应

Scheme 32. Oxidant-controlled Heck-type C-glycosylation of dihydropyrans with arylboronic acids

图式33. 钯催化二氢吡喃与芳基碘化物的Heck偶联反应

Scheme 33. Pd-catalyzed Heck coupling reactions of dihydropyrans and aryl iodides

图式34. 微波辅助钯催化合成C-芳基二氢吡喃

Scheme 34. Microwave-assisted Pd-catalyzed synthesis of C-aryldihydropyrans

图式35. 钯催化脱羧反应合成2-脱氧-C-芳基苷糖

Scheme 35. Synthesis of 2-deoxy-C-aryl glycosides by Pd-cata-lyzed decarboxylation

图式36. 钯催化三氟甲磺酸烯醇酯与二氢吡喃的立体选择性C-糖基化反应

Scheme 36. Pd-catalyzed stereoselective C-glycosylation of di-hydropyrans with enol triflates

图式37. 钯催化的脱羧烯丙基化立体选择性合成碳基二氢吡喃类衍生物

Scheme 37. Pd-catalyzed decarboxylation stereoselective synthesis of dihydropyrans

图式38. 钯催化二氢吡喃与芳基肼的氧化Heck反应

Scheme 38. Pd-catalyzed oxidative Heck reaction of dihydropyrans with arylhydrazine

图式39. “开环-闭环”的策略合成C-芳基糖

Scheme 39. “Ring Opening-Ring Closure” strategy for the synthesis of C-aryl glycosides

图式40. TEMPO促进的多米诺Heck-Suzuki芳基化反应

Scheme 40. TEMPO-promoted domino Heck-Suzuki arylation

图式41. 钯催化串联脱羧烯丙基化和Wittig反应

Scheme 41. Pd-catalyzed tandem decarboxylative allylation and Wittig reaction

图式42. 金催化串联1,3-酰氧基迁移和费里尔重排合成乙烯基二氢吡喃衍生物

Scheme 42. Au-catalyzed synthesis of vinyl dihydropyran derivatives via tandem 1,3-acyloxy migration and Ferrier rearrangement

图式43. 通过二氢吡喃和芳香胺合成2-脱氧-C-吡喃芳基糖

Scheme 43. Synthesis of 2-deoxy-C-glycosides using dihydropyrans and aromatic amines

图式44. 铱催化二氢吡喃氢芳基化反应

Scheme 44. Ir-catalyzed hydroarylation of dihydropyrans

图式45. 钯催化二氢吡喃与香豆素的立体选择性C-糖基化反应

Scheme 45. Pd-catalyzed stereoselective C-glycosylation of dihydropyrans with coumarins

图式46. 钯催化二氢吡喃与芳烃重氮盐立体选择性反应

Scheme 46. Pd-catalyzed stereoselective reaction of dihydropyrans and aromatic diazo salts

图式47. 钯催化二氢吡喃碳酸酯和芳基硼酸的反应

Scheme 47. Pd-catalyzed reaction of dihydropyran carbonates and aryl boronic acids

图式48. 其他过渡金属催化二氢吡喃的转化反应

Scheme 48. Other transition metal-catalyzed transformation reactions of dihydropyrans

图式49. 镍催化二氢吡喃的转化反应

Scheme 49. Ni-catalyzed transformation reactions of dihydropyrans

图式50. 钯催化串联环化反应

Scheme 50. Pd-catalyzed tandem cyclization

图式51. 两步法合成反式-芳基二氢吡喃酮类衍生物

Scheme 51. Synthesis of trans-aryl dihydropyranone derivatives by two-step method

图式52. 二氢吡喃酮和环状1,3-二羰基化合物的氧杂[3＋2]环加成反应

Scheme 52. Oxa-[3＋2] cycloaddition of dihydropyranones and cyclic 1,3-dicarbonyl compounds

图式53. 钯催化的[3＋2] C—C/C—N成键环化反应

Scheme 53. Pd-catalyzed [3＋2] C—C/C—N bond-formation annulation

图式54. TFAA催化合成反式二氢吡喃酮衍生物

Scheme 54. TFAA-catalyzed the synthesis of trans-dihydro-pyranone derivatives

图式55. 钯催化二氢吡喃酮与芳基硼酸的偶联反应

Scheme 55. Pd-catalyzed coupling reaction of dihydropyrans and aryl boronic acids

图式56. 钯催化烯丙基-烯丙基偶联合成香豆素基二氢吡喃酮衍生物

Scheme 56. Pd-catalyzed the synthesis of coumarin-dihydro-pyranones derivatives by allyl-allyl coupling

图式57. 钯催化(双)吲哚内酰胺和二氢吡喃的N-氨基化反应

Scheme 57. Palladium-catalyzed N-amination of di-indolectams and dihydropyrans

图式58. 钯催化磺胺的N-糖基化反应

Scheme 58. Pd-catalyzed N-glycosylation of sulfonamide

图式59. B(C6F5)3催化的N-氨基化反应

Scheme 59. B(C6F5)3-catalyzed N-amination

图式60. BF3·Et2O催化的N-氨基化反应

Scheme 60. BF3·Et2O-catalyzed N-amination

图式61. 钯催化三氯亚胺酯的重排反应

Scheme 61. Pd-catalyzed trichloroimine ester rearrangement

图式62. 配体控制三氯亚胺酯的的重排反应

Scheme 62. Ligand-controlled trichloroimine ester rearrangement

图式63. Amberlyst 15催化N-氨基化反应

Scheme 63. Amberlyst 15-catazlyed N-amination

图式64. ZnCl2/Al2O3催化N-氨基化反应

Scheme 64. ZnCl2/Al2O3-catalyzed N-amination

图式65. 路易斯酸催化合成N-氨基烯酮

Scheme 65. Lewis acid-catalyzed synthesis of N-amino enones

图式66. 钯催化脱羧烯丙基化一锅法合成β-N-咪唑基二氢吡喃衍生物

Scheme 66. Pd-catalyzed decarboxylative allylation for one-pot synthesis of β-N-imidazolyl dihydropyrans

图式67. 分子碘促进二氢吡喃与胺的氮杂-费里尔重排反应

Scheme 67. I2-promoted aza-Ferrier rearrangement of dihydropyrans with amines

图式68. 钌催化N-氨基化反应

Scheme 68. Ru-catalyzed N-amination

图式69. Zn(OTf)2催化的N-氨基化反应

Scheme 69. Zn(OTf)2-catalyzed N-amination

图式70. 钯催化合成多种N-氨基二氢吡喃衍生物

Scheme 70. Pd-catalyzed synthesis of N-amino dihydropyran derivatives

图式71. Er(OTf)3催化一锅法合成N-氨基二氢吡喃衍生物

Scheme 71. Er(OTf)3-catalyzed one-pot synthesis of N-amino dihydropyran derivatives

图式72. 钯催化立体选择性合成β-N-氨基二氢吡喃

Scheme 72. Pd-catalyzed stereoselective synthesis of β-N-amino dihydropyrans

图式73. 酰胺/胺与糖基供体的直接N-糖基化反应

Scheme 73. Direct N-glycosylation of amides/amines with gly-cal donors

图式74. 钯催化合成氮基二氢吡喃酮类衍生物

Scheme 74. Pd-catalyzed the synthesis of amino dihydropyranone derivatives

图式75. 布朗斯特酸催化合成亚砜亚胺基二氢吡喃酮类衍生物

Scheme 75. Brønsted acid-catalyzed the synthesis of sulfoximide substituted dihydropyranone derivatives

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基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展

Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification

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