Phosphorsaeure-- | 4619-09-4

• 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: Phosphorsaeure--
• 英文别名: phosphoric acid diethyl ester-(3-dimethylamino-phenyl ester)；Phosphorsaeure-diaethylester-(3-dimethylamino-phenylester)；Phosphoric acid, m-(dimethylamino)phenyl diethyl ester；[3-(dimethylamino)phenyl] diethyl phosphate
• CAS: 4619-09-4
• 化学式: C₁₂H₂₀NO₄P
• 分子量: 273.269
• InChiKey: PAIVEGSMGRDHOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  150-158 °C(Press: 0.5 Torr)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  Phosphorsaeure-- 、 碘甲烷 生成 3-diethoxyphosphoryloxy-tri-N-methyl-anilinium; iodide
  参考文献：
  名称：

  Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators

  摘要：

  Oxime-induced reactivation of phosphonylated cholinesterases (ChEs) produces charged phosphonyl pyridine oxime intermediates (POXs) that are most potent organophosphate (OP) inhibitors of ChEs. To understand the role of cationic pyridine oxime leaving groups in the enhanced anti-ChE activity of POXs, the bimolecular rate constants for the inhibition (k(i)) of acetylcholinesterases (AChE) and butyrylcholinesterases (BChE), and the rate of decomposition (k(d)) of authentic O-alkyl methylphosphonyl pyridine oximes (AlkMeP-POXs) and N,N-dimethylamidophosphoryl pyridine oximes (EDMP-POXs), were studied. Stability ranking order in aqueous solutions correlated well with the electronic features and optimized geometries that were obtained by ab initio calculations at 6-31G** basis set level. AlkMeP-POXs of the 2-pyridine oxime series were found to be 4- to 8-fold more stable (t(1/2) = 0.7 to 1.5 min) than the homologous O,O-diethylphosphoryl (DEP) oxime. Results suggest that re-inhibition of enzyme activity by POX is less likely during the reactivation of DEP-ChEs (obtained by use of DEP-containing pesticides) by certain oximes, compared to nerve agent-inhibited ChEs. The greatest inhibition was observed for the O-cyclohexyl methylphosphonyl-2PAM derivative (4.0 x 10(9) M-1 min(-1); mouse AChE) and is 10-fold higher than the k(i) of cyclosarin. Increasing the size of the O-alkyl substituent of AlkMeP-POXs had only a small to moderate effect on the ki of ChEs, signifying a major role for the cationic pyridine oxime leaving group in the inhibition reaction. The shape of plots of log k(i) vs. pK(a) of the leaving groups for AlkMeP-PAMs and DEP-PANIs, could be used as a diagnostic tool to highlight and rationalize the unique properties of the cationic moiety of pyridine oxime reactivators. (C) 2003 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0006-2952(03)00204-1
• 作为产物：
  描述：

  氰基磷酸二乙酯 、 3-羟基-N,N-二甲基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到Phosphorsaeure--
  参考文献：
  名称：

  一种用氰基膦酸二乙酯磷酸化苯酚的简便方法

  摘要：

  摘要 苯酚与氰基膦酸二乙酯在 0°C 二氯甲烷溶液中的磷酸化反应简单、快速且产率高。

  DOI：

  10.1080/00397919708005008

文献信息

• Andrews et al., Journal of the Chemical Society, 1952, p. 780,782
  作者：Andrews et al.

  DOI：——

  日期：——
• Boter,H.L.; Toet,H.J., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 1279 - 1283
  作者：Boter,H.L.、Toet,H.J.

  DOI：——

  日期：——
• Amino-aryl esters of acid phosphorus compounds
  申请人：FITCH HOWARD M

  公开号：US02759961A1

  公开（公告）日：1956-08-21
• A Convenient Method for the Phosphorylation of Phenols with Diethyl Cyanophosphonate
  作者：Angel Guzmán、Eduardo Diaz

  DOI：10.1080/00397919708005008

  日期：1997.9

  Abstract Phosphorylation of phenols with diethyl cyanophosphonate in methylene chloride solution at 0°C is an easy, rapid and good yielding reaction.

  摘要 苯酚与氰基膦酸二乙酯在 0°C 二氯甲烷溶液中的磷酸化反应简单、快速且产率高。
• Inhibition of cholinesterases with cationic phosphonyl oximes highlights distinctive properties of the charged pyridine groups of quaternary oxime reactivators
  作者：Yacov Ashani、Apurba K. Bhattacharjee、Haim Leader、Ashima Saxena、Bhupendra P. Doctor

  DOI：10.1016/s0006-2952(03)00204-1

  日期：2003.7

  Oxime-induced reactivation of phosphonylated cholinesterases (ChEs) produces charged phosphonyl pyridine oxime intermediates (POXs) that are most potent organophosphate (OP) inhibitors of ChEs. To understand the role of cationic pyridine oxime leaving groups in the enhanced anti-ChE activity of POXs, the bimolecular rate constants for the inhibition (k(i)) of acetylcholinesterases (AChE) and butyrylcholinesterases (BChE), and the rate of decomposition (k(d)) of authentic O-alkyl methylphosphonyl pyridine oximes (AlkMeP-POXs) and N,N-dimethylamidophosphoryl pyridine oximes (EDMP-POXs), were studied. Stability ranking order in aqueous solutions correlated well with the electronic features and optimized geometries that were obtained by ab initio calculations at 6-31G** basis set level. AlkMeP-POXs of the 2-pyridine oxime series were found to be 4- to 8-fold more stable (t(1/2) = 0.7 to 1.5 min) than the homologous O,O-diethylphosphoryl (DEP) oxime. Results suggest that re-inhibition of enzyme activity by POX is less likely during the reactivation of DEP-ChEs (obtained by use of DEP-containing pesticides) by certain oximes, compared to nerve agent-inhibited ChEs. The greatest inhibition was observed for the O-cyclohexyl methylphosphonyl-2PAM derivative (4.0 x 10(9) M-1 min(-1); mouse AChE) and is 10-fold higher than the k(i) of cyclosarin. Increasing the size of the O-alkyl substituent of AlkMeP-POXs had only a small to moderate effect on the ki of ChEs, signifying a major role for the cationic pyridine oxime leaving group in the inhibition reaction. The shape of plots of log k(i) vs. pK(a) of the leaving groups for AlkMeP-PAMs and DEP-PANIs, could be used as a diagnostic tool to highlight and rationalize the unique properties of the cationic moiety of pyridine oxime reactivators. (C) 2003 Elsevier Science Inc. All rights reserved.