ethyl p-nitrophenyl chloromethylphosphonate | 71790-86-8

• 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: ethyl p-nitrophenyl chloromethylphosphonate
• 英文别名: O-(4-nitrophenyl)-O-ethyl (chloromethyl)phosphonate；O-(4-nitro-phenyl) O-ethyl chloromethylphosphonate；O-ethyl O-(4-nitrophenyl) chloromethylphosphonate；O-ethyl O-(p-nitrophenyl) chloromethylphosphonate；O-ethyl-O-(p-nitrophenyl)chloromethylphosphonate；O-ethyl O-p-nitrophenyl chloromethylphosphonate；Ethyl 4-nitrophenyl (chloromethyl)phosphonate；1-[chloromethyl(ethoxy)phosphoryl]oxy-4-nitrobenzene
• CAS: 71790-86-8
• 化学式: C₉H₁₁ClNO₅P
• 分子量: 279.617
• InChiKey: VCLXXZPCUQQRDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  ethyl p-nitrophenyl chloromethylphosphonate 在 6-chloro-4-dodecyl-2-oxobenzo[e][1,2]oxaphosphinin-2-ol triethylammonium salt 、 sodium 6-chloro-4-dodecyl-2-hydroxybenzo[e]-1,2-oxaphosphinin-2-oate 2-oxide 、 水 作用下， 生成 4-硝基苯酚阴离子
  参考文献：
  名称：

  Supramolecular water systems based on the new amphiphilic phosphacoumarins: synthesis, self-organizations and reactivity

  摘要：

  Tensiometry, conductometry, dynamic light scattering, microelectrophoresis and kinetics of O-(4-nitrophenyl) O-ethyl chloromethylphosphonate hydrolysis in supramolecular water system based on 6-chloro-4-dodecyl-2-oxobenzo[e][1,2]oxaphosphinin-2-ol salts revealed that supramolecular nanoparticles structure of the system depended on counter-ion nature and substance concentration.

  DOI：

  10.1016/j.mencom.2010.05.008
• 作为产物：
  描述：

  ethyl (chloromethyl)phosphonochloridate 、 4-nitrophenol sodium salt 以 乙腈 为溶剂， 反应 2.0h， 以50%的产率得到ethyl p-nitrophenyl chloromethylphosphonate
  参考文献：
  名称：

  Blinova, G. G.; Burova, O. N.; Lavrent'ev, A. N., Journal of general chemistry of the USSR, 1986, vol. 56, # 6, p. 1126 - 1128

  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。
• Protolytic properties and reactivity of aminomethylated calix[4]resorcarenes in reactions with esters of phosphorus acids
  作者：I. S. Ryzhkina、L. A. Kudryavtseva、A. R. Mustafina、Yu. E. Morozova、E. Kh. Kazakova、K. M. Enikeev、A. I. Konovalov

  DOI：10.1007/bf02496160

  日期：1999.3

  acid-base properties and the kinetics of reactions of aminomethylated calix[4]resorcarenes (AMC) withp-nitrophenyl esters of phosphorus acids in aqueous solutions of propan-2-ol (80 vol.% PriOH) were studied by potentiometry, UV spectrophotometry, and31P NMR spectroscopy. The effect of the length of the hydrocarbon radical and substituents at the nitrogen atom on the protolytic properties and reactivity

  用电位计、紫外分光光度法研究了氨甲基化杯[4]间苯二酚(AMC)与磷酸的对硝基苯酯在丙-2-醇(80 vol.% PriOH)水溶液中的酸碱性质和反应动力学和 31 P NMR 光谱。研究了烃基的长度和氮原子上的取代基对AMC的质子分解性质和反应活性的影响。所研究的反应分两个阶段进行。在第一阶段，形成磷酸化的 AMC，在第二阶段水解成相应的酸。
• 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。
• Control of the catalytic effect of cetyltrimethylammonium bromide micelles by the addition of background electrolyte and nonionic surfactant
  作者：A. B. Mirgorodskaya、L. Ya. Zakharova、F. G. Valeeva、A. V. Zakharov、L. Z. Rizvanova、L. A. Kudryavtseva、H. E. Harlampidi、A. I. Konovalov

  DOI：10.1007/s11172-007-0312-9

  日期：2007.10

  properties (surface potential, micropolarity, etc.) of the interface of cetyltrimethylammonium bromide micelles upon the addition of a background electrolyte or the nonionic surfactant Triton X-100 decreases the rates of ion-molecular reactions, namely, alkaline hydrolysis of carboxylic acid esters and tetracoordinate phosphorus acid esters, and results in the shift of acid-base equilibria.

  添加背景电解质或非离子表面活性剂 Triton X-100 后，十六烷基三甲基溴化铵胶束界面的微观性质（表面电位、微极性等）的变化降低了离子-分子反应的速率，即碱性水解羧酸酯和四配位磷酸酯，并导致酸碱平衡的移动。
• 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。