烷基-1,1,1-三膦酸酯的合成与反应性。
Synthesis and reactivity of alkyl-1,1,1-trisphosphonate esters.
机构信息
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, United States.
出版信息
J Org Chem. 2011 Nov 4;76(21):8807-13. doi: 10.1021/jo201523w. Epub 2011 Oct 4.
Abstract
The α-trisphosphonic acid esters provide a unique spatial arrangement of three phosphonate groups and may represent an attractive motif for inhibitors of enzymes that utilize di- or triphosphate substrates. To advance studies of this unique functionality, a general route to alkyl derivatives of the parent system (R = H) has been developed. A set of new α-alkyl-1,1,1-trisphosphonate esters has been prepared through phosphinylation and subsequent oxidation of tetraethyl alkylbisphosphonates, and the reactivity of these new compounds has been studied in representative reactions that afford additional examples of this functionality.
摘要
α-三膦酸酯提供了三个膦酸酯基团的独特空间排列，可能代表了利用二膦酸酯或三磷酸酯底物的酶抑制剂的有吸引力的基序。为了推进对这种独特功能的研究，开发了一种制备母体系统（R = H）的烷基衍生物的通用途径。通过膦化和随后氧化四乙基烷基双膦酸酯，制备了一组新的α-烷基-1,1,1-三膦酸酯，并研究了这些新化合物在代表性反应中的反应性，这些反应提供了这种功能的更多实例。
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