O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(furan-2-yl)methylphosphonate | 263722-89-0

• 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: O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(furan-2-yl)methylphosphonate
• 英文别名: O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy)-1-(furan-2-yl)methylphosphonate；[dimethoxyphosphoryl(furan-2-yl)methyl] 2-(2,4-dichlorophenoxy)acetate
• CAS: 263722-89-0
• 化学式: C₁₅H₁₅Cl₂O₇P
• 分子量: 409.16
• InChiKey: IEQFSNFNURWUPF-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  487.7±45.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(furan-2-yl)methylphosphonate 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以82%的产率得到Lithium;[[2-(2,4-dichlorophenoxy)acetyl]oxy-(furan-2-yl)methyl]-methoxyphosphinate
  参考文献：
  名称：

  α-氧代膦酸单锂盐的简单和改进制备

  摘要：

  一些α-氧代磷酸单锂盐是通过简单的一步法合成的。以这种方式，α-(2,4-二氯苯氧基乙酰氧基)烷基膦酸二甲酯5可以在温和条件下转化为相应的膦酸酯单锂盐6而不影响羧酸酯基团。

  DOI：

  10.1080/10426500490474941
• 作为产物：
  描述：

  dimethyl 1-hydroxy-1-furylmethylphosphonate 、 2-(2,6-二氯苯氧基)乙酰氯 在 organic base 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以81.4%的产率得到O,O-dimethyl (2,4-dichlorophenoxyacetoxy)(furan-2-yl)methylphosphonate
  参考文献：
  名称：

  α-氧代膦酸单锂盐的简单和改进制备

  摘要：

  一些α-氧代磷酸单锂盐是通过简单的一步法合成的。以这种方式，α-(2,4-二氯苯氧基乙酰氧基)烷基膦酸二甲酯5可以在温和条件下转化为相应的膦酸酯单锂盐6而不影响羧酸酯基团。

  DOI：

  10.1080/10426500490474941

文献信息

• SIMPLE AND IMPROVED PREPARATION OF α-OXOPHOSPHONATE MONOLITHIUM SALTS
  作者：Tao Wang、Hong Wu He

  DOI：10.1080/10426500490474941

  日期：2004.10.1

  Some α-OxoPhosphonate monolithium salts were synthesized by a facile one-step procedure. In this way, α-(2,4-dichlorophenoxyacetoxy)alkyl phosphonic acid dimethyl esters 5 can be transformed into the corresponding phosophonate monolithium salts 6 without influence on the carboxylic ester group under mild conditions.

  一些α-氧代磷酸单锂盐是通过简单的一步法合成的。以这种方式，α-(2,4-二氯苯氧基乙酰氧基)烷基膦酸二甲酯5可以在温和条件下转化为相应的膦酸酯单锂盐6而不影响羧酸酯基团。
• Molecular Docking and Three-Dimensional Quantitative Structure−Activity Relationship Studies on the Binding Modes of Herbicidal 1-(Substituted Phenoxyacetoxy)alkylphosphonates to the E1 Component of Pyruvate Dehydrogenase
  作者：Hao Peng、Tao Wang、Peng Xie、Ting Chen、Hong-Wu He、Jian Wan

  DOI：10.1021/jf062730h

  日期：2007.3.1

  Molecular docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies on the title compounds were performed to explore the possible inhibitory mechanism. To determine the probable binding conformations of the title phosphonate derivatives, the most potent compound 12 was chosen as a standard template and docked into the active site of PDHc E1. On the basis of the binding conformations, highly predictive 3D-QSAR models were developed with q(2) values of 0.872 and 0.873 for comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA), respectively. The predictive abilities of these models were validated by using a set of compounds that were not included in the training set. Both the CoMFA and the CoMSIA field distributions are in good agreement with the spatial and electronic structural characteristics of the binding groove of PDHc E1 selected in this work. Mapping the 3D-QSAR models to the active site of PDHc E1 provides new insight into the protein-inhibitor interaction mechanism, which is most likely valuable and applicable for designing highly active compounds in the future.