1-Fluoro-2-[fluoro(methyl)phosphoryl]oxyethane | 1428268-20-5

• 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: 1-Fluoro-2-[fluoro(methyl)phosphoryl]oxyethane
• 英文别名: 1-fluoro-2-[fluoro(methyl)phosphoryl]oxyethane
• CAS: 1428268-20-5
• 化学式: C₃H₇F₂O₂P
• 分子量: 144.058
• InChiKey: IREOZEQWUUWVBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-bromo 4-nitrophenyl methylphosphonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 生成 1-Fluoro-2-[fluoro(methyl)phosphoryl]oxyethane 、 2-fluoroethyl 4-nitrophenyl methylphosphonate
  参考文献：
  名称：

  Synthesis and anti-acetylcholinesterase properties of novel β- and γ-substituted alkoxy organophosphonates

  摘要：

  Activated organophosphate (OP) insecticides and chemical agents inhibit acetylcholinesterase (AChE) to form OP-AChE adducts. Whereas the structure of the OP correlates with the rate of inhibition, the structure of the OP-AChE adduct influences the rate at which post-inhibitory reactivation or aging phenomena occurs. In this report, we prepared a panel of beta-substituted ethoxy and gamma-substituted propoxy phosphonoesters of the type p-NO2PhO-P(X)(R)[(O(CH2)(n)Z] (R = Me, Et; X = O, S; n = 2, 3; Z = halogen, OTs) and examined the inhibition of three AChEs by select structures in the panel. The beta-fluoroethoxy methylphosphonate analog (R = Me, Z = F, n = 2) was the most potent anti-AChE compound comparable (k(i); similar to 6 x 10(6) M-1 min(-1)) to paraoxon against EEAChE. Analogs with Z = Br, I, or OTs were weak inhibitors of the AChEs, and methyl phosphonates (R = Me) were more potent than the corresponding ethyl phosphonates (R = Et). As expected, analogs with a thionate linkage (P=S) were poor inhibitors of the AChEs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.010

文献信息

• Synthesis and anti-acetylcholinesterase properties of novel β- and γ-substituted alkoxy organophosphonates
  作者：S. Kaleem Ahmed、Yamina Belabassi、Lakshmi Sankaranarayanan、Chih-Kai Chao、John M. Gerdes、Charles M. Thompson

  DOI：10.1016/j.bmcl.2013.02.010

  日期：2013.4

  Activated organophosphate (OP) insecticides and chemical agents inhibit acetylcholinesterase (AChE) to form OP-AChE adducts. Whereas the structure of the OP correlates with the rate of inhibition, the structure of the OP-AChE adduct influences the rate at which post-inhibitory reactivation or aging phenomena occurs. In this report, we prepared a panel of beta-substituted ethoxy and gamma-substituted propoxy phosphonoesters of the type p-NO2PhO-P(X)(R)[(O(CH2)(n)Z] (R = Me, Et; X = O, S; n = 2, 3; Z = halogen, OTs) and examined the inhibition of three AChEs by select structures in the panel. The beta-fluoroethoxy methylphosphonate analog (R = Me, Z = F, n = 2) was the most potent anti-AChE compound comparable (k(i); similar to 6 x 10(6) M-1 min(-1)) to paraoxon against EEAChE. Analogs with Z = Br, I, or OTs were weak inhibitors of the AChEs, and methyl phosphonates (R = Me) were more potent than the corresponding ethyl phosphonates (R = Et). As expected, analogs with a thionate linkage (P=S) were poor inhibitors of the AChEs. (C) 2013 Elsevier Ltd. All rights reserved.