Chloromethyl(ethoxy)phosphinate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Chloromethyl(ethoxy)phosphinate
• 化学式: C₃H₇ClO₃P
• 分子量: 157.514
• InChiKey: QLDHAICZNLDAEK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl p-nitrophenyl chloromethylphosphonate 在 sodium hydroxide 、 水 、 溴代十六烷基吡啶 作用下， 生成 Chloromethyl(ethoxy)phosphinate
  参考文献：
  名称：

  Zakharova; Shagidullina; Valeeva, Russian Journal of Physical Chemistry, 2000, vol. 74, # 11, p. 1821 - 1824

  摘要：

  DOI：

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。
• Catalytic effect of supramolecular system based on cationic surfactant and monopodands in nucleophilic substitution of phosphorus esters
  作者：F. G. Valeeva、A. V. Zakharov、M. A. Voronin、L. Ya. Zakharova、L. A. Kudryavtseva、O. G. Isaikina、A. A. Kalinin、V. A. Mamedov

  DOI：10.1023/b:rucb.0000046255.85293.5f

  日期：2004.7

  podands with terminal quinoxaline fragments of rings and their influence on both the micellization properties of cetyltrimethylammonium bromide in a water—DMF solution and kinetics of basic hydrolysis of O-p-nitrophenyl O-ethyl chloromethylphosphonate and O-p-nitrophenyl O-hexyl chloromethylphosphonate in the absence and presence of surfactants. The mechanism of the podand effect on the reaction rate

  数据显示了具有环的末端喹喔啉片段的 podands 的合成及其对十六烷基三甲基溴化铵在水 - DMF 溶液中的胶束化特性和 Op-硝基苯基 O-乙基氯甲基膦酸酯和 Op-硝基苯基 O 的碱性水解动力学的影响-氯甲基膦酸己基酯在表面活性剂不存在和存在下。podand效应对反应速率的作用机制取决于膦酸酯和podand的结构。1,8-Bis(3-ethyl-1,2-dihydro-2-oxoquinoxalin-1-yl)-3,6-dioxoctane 抑制底物的碱性水解 3-4 倍。在表面活性剂的胶束溶液中，观察到反应速率常数加速了大约 20 倍。当 podand 添加到胶束溶液中时，观察到的速率常数会降低。多组分系统的催化作用是由于反应物的浓缩。胶束微环境可以对膦酸盐的反应性产生积极和消极的影响。
• The salt effect in the alkaline hydrolysis ofO-ethylO-(p-nitrophenyl) chloromethylphosphonate catalyzed by cetylpyridinium bromide
  作者：L. Ya. Zakharova、L. A. Kudryavtseva、A. I. Konovalov

  DOI：10.1007/bf02494486

  日期：1998.10

  The alkaline hydrolysis ofO-ethylO-(p-nitrophenyl) chloromethylphosphonate catalyzed by the micelles of cetylpyridinium bromide is inhibited on addition of KCl, K Br, or sodium salicylate (NaSal). This is caused by both a decrease in the nucleophile concentration in micelles owing to a reduction in the surface potential and a change in the micellar structure and properties.

  添加 KCl、K Br 或水杨酸钠 (NaSal) 后，由溴化十六烷基吡啶鎓胶束催化的 O-乙基 O-(对硝基苯基) 氯甲基膦酸酯的碱性水解受到抑制。这是由于表面电位降低导致胶束中亲核试剂浓度降低以及胶束结构和性质发生变化造成的。
• Alkaline hydrolysis of ethylp-nitrophenyl chloromethylphosphonate in the reverse micellar AOT—decane—water system
  作者：L. Ya. Zakharova、F. G. Valeeva、L. A. Kudryavtseva、A. I. Konovalov、N. L. Zakharchenko、Yu. F. Zuev、V. D. Fedotov

  DOI：10.1007/bf02498266

  日期：1999.12

  The influence of cluster formation of micelles on the rate of alkaline hydrolysis of ethylp-nitrophenyl chloromethylphosphonate in the reverse micellar sodium bis(2-ethylhexyl) sulfosuccinate (AOT)—decane—water system was found. The applicability of the pseudo-phase model of micellar catalysis below and above the percolation threshold was shown.

  发现了胶束簇形成对双(2-乙基己基)磺基琥珀酸钠(AOT)-癸烷-水反胶束体系中对硝基苯基氯甲基膦酸乙酯碱水解速率的影响。显示了低于和高于渗透阈值的胶束催化假相模型的适用性。
• 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。