The Synthesis of Amino-substituted Phosphonic Acids. III1
The Synthesis of Amino-substituted Phosphonic Acids. III1
复制标题
氨基取代的膦酸的合成。
DOI：
10.1021/ja01117a040
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发表时间：
1947
影响因子：
15
通讯作者：
G. M. Kosolapoff
中科院分区：
文献类型：
--
作者：
M. Chalmers;G. M. Kosolapoff
利用亚磷酸二烷基酯、氨和醛的相互作用，合成了下列碳原子上含N-氨基的膦酸二烷基酯：二乙基和N-α-氨基苄基膦酸二乙酯、二乙基-氨基乙基膦酸二乙酯、二乙基-氨基丙基膦酸二乙酯、二乙基-α-甲氧基苄基-α-氨基膦酸二乙酯、二乙基-β-羟基苄基-α-氨基膦酸二乙酯、二乙基-α-羟基苄基-α-氨基膦酸二乙酯和二乙基-β-苯基乙基-α-氨基膦酸二乙酯。将酯转化为游离氨基膦酸，其特征在于。获得了关于氨甲基膦酸的制备的其它细节。在我们关于分子中含有氨基的膦酸的合成和性质测定的工作的继续中，我们研究了在亚磷酸二烷基酯、羰基化合物和氨之间发生的Mannich型反应，最近Kabachnik和Medved在几个例子中报道了一个以酮为羰基化合物的反应。该反应可概括地由以下方程式表示：
The interaction of dialkyl phosphites, ammonia and aldehydes was employed for the synthesis of thefollowing dialkyl phosphonates which contain^ n amino group on the first carbon atom: diethyl and dibutyl a-aminobenzylphosphonates, diethyl-aminoethylphosphonate, diethyl-aminopropylphosphonate, diethyl^-methoxybenzyl-a-aminophosphonate, diethyl£-hydroxybenzyl-a-aminophosphonate, diethyl o-hydroxybenzyl-a-aminophosphonateand diethyl/3-phenylethyltt-aminophosphonate. The esters were converted to the free aminophosphonic acids, which were characterized. Additional details concerning the preparation of aminomethylphosphonic acid were obtained.In continuation of our work on the synthesis and the determination of properties of phosphonic acids that contain an amino group in the molecule we examined the Mannich-type reaction which takes place between dialkyl phosphites, carbonyl compounds and ammonia, a reaction which was re-ported recently by Kabachnik and Medved in sev-eral examples involving ketones as the carbonyl compounds. The reaction can be summarily represented by the equation