<br>膦酸：制备和应用。,Beilstein Journal of Organic Chemistry

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膦酸：制备和应用。
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2017-10-20 , DOI: 10.3762/bjoc.13.219
Charlotte M Sevrain ₁ , Mathieu Berchel ₁ , Hélène Couthon ₁ , Paul-Alain Jaffrès ₁

Affiliation

膦酸官能团的特征是一个磷原子与三个氧原子（两个羟基和一个 P=O 双键）和一个碳原子键合，由于其结构与磷酸酯部分相似，因此被用于许多应用。其配位或超分子特性。膦酸因其生物活性特性（药物、前药）而被用于骨靶向、超分子或混合材料的设计、表面功能化、分析目的、医学成像或作为磷酸抗原。这些应用涵盖了化学、生物学和物理学等众多研究领域，因此膦酸的合成成为许多研究项目的决定性问题。本综述首先概述了膦酸的不同应用领域，并通过主要选取过去 20 年的研究进行了说明。此外，该综述报告了可用于从二烷基或二芳基膦酸酯、从二氯膦或二氯氧化膦、从膦二酰胺或通过次膦酸的氧化合成膦酸的不同方法。还研究了利用亚磷酸 (H3PO3) 并在形成 PC 键的同时产生膦酸官能团的直接方法。在所有这些方法中，二烷基膦酸酯在酸性条件 (HCl) 下脱烷基或使用 McKenna 程序（利用溴三甲基硅烷然后进行甲醇分解的两步反应）构成了制备膦酸的最佳方法。

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Phosphonic acid: preparation and applications.

The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P-C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

更新日期：2019-11-01

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