Phosphodiester Alkylation with a Quinone Methide.
Phosphodiester Alkylation with a Quinone Methide.
复制标题
磷酸二酯与甲基醌的烷基化。
DOI：
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发表时间：
1999
影响因子：
3.6
通讯作者：
K. Turnbull
中科院分区：
文献类型：
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作者：
Qibing Zhou;K. Turnbull
尽管有大量的研究涉及DNA烷基化和醌甲基化物产生化合物的裂解，但还没有关于磷酸二酯与醌甲基化物烷基化的报道。我们研究了磷酸二烷基酯与对苯醌甲基化物的反应，以确定烷基化产生磷酸三烷基酯的可能性。这些研究表明，磷酸二酯在布朗斯台德酸的促进下可以被对苯醌甲基化物烷基化。布朗斯台德酸的作用是充分活化对苯醌甲基化物，使磷酸二酯加成反应发生。已发现磷酸二酯的烷基取代基在所检查的反应条件下影响磷酸二烷基酯的反应性。平衡转化率高达83%的磷酸三烷基酯的形成已经实现。
Despite the wide array of studies involving DNA alkylation and cleavage with quinone methide generating compounds, there have been no reports on the alkylation of phosphodiesters with quinone methides. We have investigated the reaction of dialkyl phosphates with a p-quinone methide in order to determine the potential for alkylation to produce trialkyphosphates. These studies have revealed that a phosphodiester can be alkylated with a p-quinone methide when promoted by a Brønsted acid. The role of the Brønsted acid is to sufficiently activate the p-quinone methide to allow phosphodiester addition to occur. The alkyl substituents of the phosphodiester have been found to effect the reactivity of the dialkyl phosphate under the reaction conditions examined. Equilibrium conversions up to 83% trialkyl phosphate formation have been achieved.