芳基、烷基磷酸混酯类化合物的合成方法研究进展

doi:10.6023/cjoc202105056

摘要/Abstract

芳基、烷基磷酸混酯是一类重要的有机磷化物, 广泛应用于生物、医药、农药、高分子以及材料科学等众多领域, 具有广阔的发展前景. 含磷基团所特有的物理、化学以及生物性质, 为其结构修饰、衍生化以及应用领域的拓展提供了更多可能, 因此, 该类化合物合成方法的研究具有重要的理论和现实意义. 综述了过去几十年芳基、烷基磷酸混酯化合物制备方法的研究进展, 列举了其应用实例, 分类总结了多种不同类型的含磷试剂向目标化合物转化的实验方法和发展历程, 选择性地探讨了反应的特点、机理以及在合成中的应用, 希望该综述能够为磷酸混酯类化合物新型制备方法的开发提供参考, 为相关领域的学者、研究生以及其他人员提供一些有益借鉴.

关键词: 合成方法, 磷酸混酯, 有机磷化物

Aryl and alkyl mixed phosphates are very important phosphorus containing organic compounds, which are widely used in many fields, such as biology, medicine, pesticide, polymer, and material science. The unique physical, chemical, and biological properties of phosphorus-based motifs provide more possibilities for their structural modification, derivatization, and potential application. Therefore, the research on the preparation of these compounds has important theoretical and practical significance. In this paper, the research progress of the synthesis methodologies of aryl and alkyl mixed phosphate in the past few decades is reviewed. The application examples are listed. The experimental methods and development process of the conversion of various kinds of phosphorus containing reagents to target compounds are summarized. The characteristics, mechanism, and application of the reaction are discussed selectively as well. We hope that this review can provide a reference for the development of new preparation protocols of mixed phosphate, and provide some useful references for scholars, graduate students, and others in the related fields.

Key words: synthetic method, mixed phosphate, organic phosphorus compound

引用此文

焦林郁, 于华, 宁资慧, 李卓. 芳基、烷基磷酸混酯类化合物的合成方法研究进展[J]. 有机化学, 2021, 41(11): 4180-4191.

Linyu Jiao, Hua Yu, Zihui Ning, Zhuo Li. Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4180-4191.

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图/表 44

图1. 芳基、烷基磷酸混酯在农业方面的应用

Figure 1. Application of aryl and alkyl mixed phosphates in agriculture

图2. 磷酸混酯类脂质前体药物

Figure 2. Aryl and alkyl mixed phosphates as lipid prodrug

图3. 芳基、烷基磷酸混酯化合物在生物医药方面的应用

Figure 3. Application of aryl and alkyl mixed phosphates in biomedicine

图4. 磷酸混酯化合物在阻燃剂方面的应用

Figure 4. Application of aryl and alkyl mixed phosphates in flame retardant

图5. 磷酸混酯类含氟表面活性剂

Figure 5. Mixed phosphates as fluorosurfactant

图式1. 经典Atherton-Todd反应通式

Scheme 1. Classical Atherton-Todd reaction formula

图式2. 黄酮化合物的磷酰化反应

Scheme 2. Phosphorylation of flavonoids

图式3. [3,3]-σ迁移重排制备磷酸混酯

Scheme 3. [3,3]-σ migratory rearrangement to prepare mixed phosphates

图式4. CuCl2催化下的Atherton-Todd反应制备磷酸酯

Scheme 4. Preparation of phosphate through Atherton-Todd reaction catalyzed by CuCl2

图式5. TCICA作用下的一锅法合成磷酸混酯

Scheme 5. One-pot synthesis of mixed phosphate under TCICA

图式6. LiI/TBHP催化下的芳基、烷基磷酸混酯的合成

Scheme 6. Synthesis of aryl and alkyl mixed phosphates catalyzed by LiI/TBHP

图式7. 吡啶促进的磷酰氯和乙醇的酯化反应

Scheme 7. Pyridine promoted esterification of phosphoryl chloride and ethanol

图式8. 吡啶促进的二苯基磷酰氯和四氢糠醇的酯化反应

Scheme 8. Pyridine promoted esterification of diphenylphosphoryl chloride and tetrahydrofurfuryl alcohol

图式9. 钛基Lewis酸在磷酸混酯合成中的催化机理

Scheme 9. Catalytic mechanism of titanium-based Lewis acid in the synthesis of mixed phosphates

图式10. MoOCl4催化磷酸混酯合成的反应机理

Scheme 10. Reaction mechanism of MoOCl4 catalyzed synthesis of mixed phosphates

图式11. 磷酸纤维素二苯酯在离子液体中的合成

Scheme 11. Synthesis of cellulose diphenyl phosphate in ionic liquid

图式12. 基于聚乙二醇链的催化剂在合成磷酸混酯中的应用

Scheme 12. Application of catalysts based on polyethylene glycol chains in the synthesis of mixed phosphates

图式13. 与聚合物结合的三氮烯催化P(O)—OH合成磷酸混酯类化合物

Scheme 13. Triazene combined with polymer catalyzed P(O)—OH synthesis of mixed phosphatess

图式14. SiO2—Cl催化的以P(O)—OH化合物的酯化反应

Scheme 14. Esterification of P(O)—OH compound catalyzed by SiO2—Cl

图式15. p-TsOH-Celite催化的以P(O)—OH化合物的酯化反应

Scheme 15. p-TsOH-celite catalyzed esterification reaction with P(O)—OH compound

图式16. PPh3和三氯乙腈作用下经“一锅法”合成磷酸混酯

Scheme 16. Synthesis of mixed phosphates by “one-pot reaction” with the promotion of PPh3 and trichloroacetonitrile

图式17. 碱促进的二苯基磷酸与苄溴反应制备磷酸混酯

Scheme 17. Alkali-promoted reaction of diphenylphosphoric acid with benzyl bromide to prepare mixed phosphates

图式18. P(O)—OH和脂肪醇以及二芳基碘鎓盐的酯化反应

Scheme 18. Esterification of P(O)—OH with aliphatic alcohols and diaryliodonium salts

图式19. 亚磷酸酯经氧化和分解制备磷酸混酯

Scheme 19. Preparation of mixed phosphates by oxidation and decomposition of phosphite

图式20. 光诱导的芳基、烷基磷酸混酯的催化制备

Scheme 20. Catalytic preparation of light-induced aryl and alkyl mixed phosphates

图式21. 磷酸三芳基酯在锌配合物作用下的醇解反应

Scheme 21. Alcoholysis of triaryl phosphate under the action of zinc complex

图式22. 铝卟啉二聚体催化的磷酸三芳基酯的醇解反应

Scheme 22. Alcoholysis of triaryl phosphate catalyzed by aluminum porphyrin dimer

图式23. UIO-66催化的磷酸三芳基酯的水解和醇解反应

Scheme 23. Hydrolysis and alcoholysis of triaryl phosphate catalyzed by UIO-66

图式24. Tf2O/吡啶促进的连续酯交换反应

Scheme 24. Tf2O/pyridine promoted continuous transesterification reaction

图式25. P2O5促进的磷酸三乙酯的酯交换反应

Scheme 25. Transesterification of triethyl phosphate promoted by P2O5

图式26. 叠氮磷酸二苯酯和脂肪醇在铜作用下的催化转化

Scheme 26. Catalytic conversion of diphenyl azide phosphate and fatty alcohol under the action of copper

图式27. 叠氮磷酸二苯酯和脂肪醇在锌作用下的催化转化

Scheme 27. Catalytic conversion of diphenyl azide phosphate and aliphatic alcohol under the action of zinc

图式28. 叠氮磷酸二苯酯在多相体系下的催化转化

Scheme 28. Catalytic conversion of diphenyl azide phosphate in heterogeneous system

图式29. 磷酰吡啶鎓盐中间体在磷酸混酯合成中的应用

Scheme 29. Application of phosphorylpyridinium salt intermediate in the synthesis of mixed phosphates

图式30. 高压汞灯条件下磷酰吡啶鎓盐在磷酸混酯合成中的应用

Scheme 30. Application of phosphorylpyridinium salt in the synthesis of mixed phosphates under the condition of high pressure mercury lamp

图式31. 基于NCT的新型磷酰化试剂在磷酸混酯合成中的应用

Scheme 31. Application of NCT-based new phosphorylation reagents in the synthesis of mixed phosphates

图式32. NCT与磷酰氯制备磷酰胺化合物

Scheme 32. Preparation of phosphoramide compounds from NCT and phosphoryl chloride

图式33. 噁唑烷酮与磷酰氯合成新型磷酰化试剂

Scheme 33. Synthesis of novel phosphorylation reagents from oxazolidinone and phosphoryl chloride

图式34. 含有噁唑烷酮的新型磷酰化试剂在磷酸酯合成中的应用

Scheme 34. Application of new phosphorylation reagents containing oxazolidinone in the synthesis of phosphates

图式35. 含有噁唑烷酮的新型磷酰化试剂在铜盐作用下的催化转化

Scheme 35. Catalytic conversion of a novel phosphorylation reagent containing oxazolidinone under the action of copper salt

图式36. 苯并三唑类磷酰化试剂的转化方案

Scheme 36. Conversion scheme of benzotriazole phosphorylation reagent

图式37. 苯并三唑类磷酰化试剂在磷酸混酯合成中的应用

Scheme 37. Application of benzotriazole phosphorylation reagents in the synthesis of mixed phosphates

图式38. DEPC的合成路线

Scheme 38. Synthetic route of DEPC

图式39. 氰基膦酸二乙酯与对氯苯酚的酯化反应

Scheme 39. Esterification reaction of diethyl cyanophosphonate with p-chlorophenol

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