O-(4-nitrophenyl)-O-butyl (chloromethyl)phosphonate | 81260-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(4-nitrophenyl)-O-butyl (chloromethyl)phosphonate
• 英文别名: O-butyl-O-4-nitrophenylchloromethyl phosphonate；O-p-nitrophenyl-O-butylchloromethyl phosphonate；butyl p-nitrophenyl(chloromethyl)phosphonate；4-nitrophenyl butyl chloromethylphosphonate；p-nitrophenyl butyl chloromethylphosphonate；4-nitrophenyl butylchloromethylphosphonate；Butyl 4-nitrophenyl (chloromethyl)phosphonate；1-[butoxy(chloromethyl)phosphoryl]oxy-4-nitrobenzene
• CAS: 81260-41-5
• 化学式: C₁₁H₁₅ClNO₅P
• 分子量: 307.671
• InChiKey: MGHLMAOUZOUYNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-(4-nitrophenyl)-O-butyl (chloromethyl)phosphonate 在 1-hexadecyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide 作用下， 以 aq. buffer 为溶剂， 生成 Chlormethanphosphonsaeure-mono-n-butylester
  参考文献：
  名称：

  基于1-烷基-4-氮杂-1-氮杂双环[2.2.2]辛烷溴化物金属配合物的催化体系

  摘要：

  摘要基于1-烷基-4-氮杂-1-氮杂双环[2.2.2]辛烷溴化物（Alk = C n H 2 n +1，n = 16，18）与硝酸镧的络合物的超分子体系的催化活性4-硝基苯基-O-烷基氯甲基膦酸酯的水解分解反应（Alk = C n H 2 n +1，n= 4、6）。发现由于各种尺寸和类型（小胶束和较大的超分子结构）的纳米级聚集体的形成而促进了反应，其有效地结合了试剂。膦酸酯与聚集体的结合常数大于三个或四个数量级。与配体相比，金属络合物体系的催化活性在溶液中的两亲物浓度较低时表现出来。

  DOI：

  10.1134/s0023158420010140

文献信息

• Self‐Assembled Quaternary Ammonium‐Containing Comb‐Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter‐Ions
  作者：Tatiana N. Pashirova、Petr A. Fetin、Alexey A. Lezov、Matvey V. Kadnikov、Farida G. Valeeva、Evgenia A. Burilova、Alexander Yu. Bilibin、Ivan M. Zorin

  DOI：10.1002/cplu.202000417

  日期：2020.8

  concentration, particle sizes and solubilization properties toward Orange OT were determined. Self‐assemblies organized by poly(11‐acryloyloxyundecyltrimethyl ammonium) bromide successfully catalyze the hydrolysis of 4‐nitrophenyl butylchloromethylphosphonate up to two orders of magnitude compared to aqueous alkaline hydrolysis. The development of these catalysts is promising for industrial applications

  这项工作的目的是提高催化体系对膦酸的4-硝基苯基酯进行水解裂解的效率。含季铵的梳状聚电解质（“聚合的胶束”）具有酯可裂解的片段和较低的聚集阈值，被用作催化剂。聚（11-acryloyloxyundecylammonium）具有不同抗衡离子（BR表面活性剂的合成-，NO 3 -，CH 3 Ç 6 ħ 4 SO 3 -）和头基是通过胶束自由基聚合实现的。测定分子量，临界缔合浓度，粒度和对橙色OT的增溶性能。与碱性水溶液水解相比，由聚（11-丙烯酰氧基十一烷基三甲基铵）溴组成的自组装成功地催化了4-硝基苯基丁基氯甲基膦酸酯的水解，最多可提高两个数量级。这些催化剂的开发对于工业应用和有机磷化合物的脱毒很有希望。
• Catalysis of the hydrolysis of esters of phosphorus acids byn-decylammonium chloride /n-decylamine mixed micelles
  作者：R. F. Bakeeva、L. A. Kudryameva、V. E. Bel'skii、S. B. Fedorov、B. E. Ivanov

  DOI：10.1007/bf01457772

  日期：1996.8

  The effect ofn-decylammonium chloride/n-decylamine mixed micelles on the rate of hydrolysis of aryl esters of acids of four-coordinate phosphorus was studied spectrophotometrically. The shape of the concentration curves is characteristic of the micellar catalysis reactions. The binding constants of the substrate, critical micelle concentrations, and the rate constants in the micellar phase were determined

  采用分光光度法研究了正癸基氯化铵/正癸胺混合胶束对四配位磷酸芳基酯水解速率的影响。浓度曲线的形状是胶束催化反应的特征。确定了底物的结合常数、临界胶束浓度和胶束相中的速率常数。显示了基板结构对这些参数的特定影响。
• The influence of the structure of tetracoordinate phosphorus acid esters on the catalytic effect of the sodium dodecyl sulfate-hexanol-water ternary reverse micellar system
  作者：L. Ya. Zakharova、F. G. Valeeva、R. A. Shagidullina、L. A. Kudryavtseva

  DOI：10.1007/bf02495077

  日期：2000.8

  The catalytic effect of the sodium dodecyl sulfate-hexanol-water ternary reverse micellar system in the alkaline hydrolysis ofO-alkylO′-aryl chloromethylphosphonates as a function of the substrate structure was studied. The micellar effect is mainly determined by a change in the electronic properties of the substituents, while the hydrophobicity plays a secondary role. The kinetic data were examined

  研究了十二烷基硫酸钠-己醇-水三元反胶束体系对O-烷基O'-芳基氯甲基膦酸酯碱水解的催化作用作为底物结构的函数。胶束效应主要由取代基电子性质的变化决定，而疏水性起次要作用。在胶束催化假相模型的框架内检查动力学数据。计算了表层反应的速率常数和反应物的分配常数。
• Catalytic properties of polymer-colloid complexes based on polyethyleneimines and mono- and diquaternized 1,4-diazabicyclo[2.2.2]octane derivatives in the hydrolysis of phosphorus acids esters
  作者：T. N. Pashirova、E. P. Zhil´tsova、S. S. Lukashenko、L. Ya. Zakharova、A. I. Konovalov

  DOI：10.1007/s11172-015-1242-6

  日期：2015.12

  polyethyleneimines, mono- (MQD) and diquaternized (DQD) hexadecyl derivatives of 1,4-diazabicyclo[2.2.2]octane, and mixed polymercolloid systems based thereon catalyze the hydrolysis of p-nitrophenyl alkyl chloromethylphosphonates. The catalysis efficiency depends on the structures of substrate, 1,4-diazabicyclo-[2.2.2]octane derivatives, and polyethyleneimine, pH of the medium, and the temperature. In the case

  通过分光光度法确定聚乙烯亚胺、1,4-二氮杂双环[2.2.2]辛烷的单(MQD)和双季铵化(DQD)十六烷基衍生物以及基于其的混合聚合物胶体系统催化对硝基苯基烷基氯甲基膦酸酯的水解。催化效率取决于底物、1,4-二氮杂双环-[2.2.2]辛烷衍生物和聚乙烯亚胺的结构、介质的pH值和温度。在MQD的情况下，随着膦酸酯烷基的长度从R = OEt增加到R = OC6H13，催化效果从20倍变为80倍；与 MQD 相比，DQD 表现出较低的催化活性。
• Supramolecular catalytic systems based on 1, 4-diazabicyclo[2.2.2]octane, its alkylated quaternary derivatives, and lanthanum nitrate
  作者：E. P. Zhiltsova、S. S. Lukashenko、T. N. Pashirova、L. Ya. Zakharova、A. I. Konovalov

  DOI：10.1007/s11172-015-1208-8

  日期：2015.11

  used to study the catalytic effects of the systems composed of N-monoand N, N-dialkylated 1, 4-diazabicyclo[2.2.2]octanes and lanthanum nitrate on the hydrolysis rate of O-alkyl O-4-nitrophenyl chloromethylphosphonates (Alk = Et, Bun, and n-hexyl). The mechanism of action and efficiency of the catalytic system depend on the structure of the heterocycle, its propensity to aggregation and complexation

  采用分光光度法研究了N-单和N,N-二烷基化1,4-二氮杂双环[2.2.2]辛烷和硝酸镧对O-烷基O-4-硝基苯基氯甲基膦酸酯水解速率的催化作用（ Alk = Et、Bun 和正己基）。催化体系的作用机制和效率取决于杂环的结构、其与镧阳离子聚集和络合的倾向以及溶液中组分的相对含量。在 1, 4-二氮杂双环 [2.2.2] 辛烷和硝酸镧的阳离子单烷基化衍生物的胶束溶液中实现了最大的催化效果（水解速率常数增加了约 115 倍）。