7-[Dimethylamino(ethoxy)phosphoryl]oxy-4-(trifluoromethyl)chromen-2-one | 934743-99-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-[Dimethylamino(ethoxy)phosphoryl]oxy-4-(trifluoromethyl)chromen-2-one
• CAS: 934743-99-4
• 化学式: C₁₄H₁₅F₃NO₅P
• 分子量: 365.246
• InChiKey: UNAFZUKZHMNVIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-羟基-4-三氟甲基香豆素 、 N-[氯(乙氧基)磷酰基]-N-甲基甲胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以52%的产率得到7-[Dimethylamino(ethoxy)phosphoryl]oxy-4-(trifluoromethyl)chromen-2-one
  参考文献：
  名称：

  Synthesis and anticholinesterase activity of some new fluorogenic analogues of organophosphorus nerve agents

  摘要：

  Eighteen new fluorogenic analogues of organophosphorus nerve agents were synthesised and characterised. They included analogues of tabun, sarin, cyclosarin, soman, VX, and Russian VX, with the 7-oxy-4-methylcoumarin or 7-oxy-4-(trifluoromethyl)coumarin leaving group. These analogues inhibited acetylcholinesterase (AChE) effectively in vitro and therefore have potential as tools for the identification of novel organophosphatases in biological systems. Analogues of VX and Russian VX with the 7-amino-4-methylcoumarin group, although poor AChE inhibitors, may have utility for screening enzyme libraries for phosphoramidases capable of cleaving P-N bonds. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.07.017

文献信息

• Synthesis and anticholinesterase activity of some new fluorogenic analogues of organophosphorus nerve agents
  作者：Christopher M. Timperley、Krystal E. Casey、Stuart Notman、David J. Sellers、Nancy E. Williams、Nichola H. Williams、Gareth R. Williams

  DOI：10.1016/j.jfluchem.2006.07.017

  日期：2006.12

  Eighteen new fluorogenic analogues of organophosphorus nerve agents were synthesised and characterised. They included analogues of tabun, sarin, cyclosarin, soman, VX, and Russian VX, with the 7-oxy-4-methylcoumarin or 7-oxy-4-(trifluoromethyl)coumarin leaving group. These analogues inhibited acetylcholinesterase (AChE) effectively in vitro and therefore have potential as tools for the identification of novel organophosphatases in biological systems. Analogues of VX and Russian VX with the 7-amino-4-methylcoumarin group, although poor AChE inhibitors, may have utility for screening enzyme libraries for phosphoramidases capable of cleaving P-N bonds. (c) 2006 Elsevier B.V. All rights reserved.