O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)propylphosphonate | 254888-82-9

• 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 α-(2,4-dichlorophenoxyacetoxy)propylphosphonate
• 英文别名: 1-Dimethoxyphosphorylpropyl 2-(2,4-dichlorophenoxy)acetate
• CAS: 254888-82-9
• 化学式: C₁₃H₁₇Cl₂O₆P
• 分子量: 371.154
• InChiKey: REFVXEBOWZUQMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)propylphosphonate 在 potassium iodide 作用下， 反应 12.0h， 以52%的产率得到potassium O-methyl-1-(2,4-dichlorophenoxyacetoxy)-propylphosphonate
  参考文献：
  名称：

  Synthesis and herbicidal activities of methyl-1-(2,4-dichlorophenoxyacetoxy)alkylphosphonate monosalts

  摘要：

  A series of 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5 and its corresponding phosphonate monosalts 6 were synthesized as potential herbicide. The phosphonate monosalts can be prepared from 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5, which were synthesized by the condensation of O,O-dimethyl-1-hydroxyalkylphosphonates with dichlorophenoxyacetic chloride. This method provides a simple and efficient procedure for the synthesis of phosphonate derivatives containing sensitive groups to acid, base or water such as carboxylate ester bond; and the herbicidal activity of title compounds was evaluated in a set of experiments in greenhouse. Most of the compounds exhibited notable herbicidal activity. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.01.061
• 作为产物：
  描述：

  2,4-二氯苯氧乙酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)propylphosphonate
  参考文献：
  名称：

  1-(取代苯氧基乙酰氧基)烷基膦酸氢钠的合成及除草活性

  摘要：

  摘要 设计合成了一系列1-(取代苯氧基乙酰氧基)烷基膦酸氢钠。除草活性试验表明，大多数膦酸盐（8）对阔叶杂草具有优异的芽后除草活性。特别是8f和8g对油菜和苋菜的除草活性最好，抑菌率达95%以上。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要

  DOI：

  10.1080/10426507.2012.717147

文献信息

• Synthesis and Dealkylation of 1-(Dichloro-Phenoxyacetoxy)Alkyl Phosphonates
  作者：Hongwu He、Xufeng Liu、Liming Hu、Siquan Wang、Zhaojie Liu

  DOI：10.1080/10426509908546324

  日期：1999.1.1

  Using the silylation procedure with chlorotrimethylsilane/sodium iodide followed by alcoholysis, 1-(dichlorophenoxy acetoxy)alkyl phosphonic acid dimethyl esters can be transformed into the parent phosphonic acids without influence on carboxylate ester group.

  使用三甲基氯硅烷/碘化钠的硅烷化程序，然后进行醇解，可以将 1-（二氯苯氧基乙酰氧基）烷基膦酸二甲酯转化为母体膦酸，而不会影响羧酸酯基团。
• Synthesis and Herbicidal Activities of Lithium or Potassium Hydrogen 1-(Substituted Phenoxyacetoxy)Alkylphosphonates
  作者：Hao Peng、Qingwu Long、Xiaoyan Deng、Hongwu He

  DOI：10.1080/10426507.2013.797415

  日期：2013.12.1

  Abstract A series of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates were designed and synthesized. All the title compounds were identified by IR, 1H NMR, and 31P NMR, some of them were further analyzed by MS and elemental analyses. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against

  摘要 设计合成了一系列1-(取代苯氧基乙酰氧基)烷基膦酸锂或氢钾。所有标题化合物均通过 IR、1H NMR 和 31P NMR 进行鉴定，其中一些进一步通过 MS 和元素分析进行​​分析。除草活性试验表明，大多数膦酸盐（8）对阔叶杂草具有优异的芽后除草活性。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Studies of <i>O</i>,<i>O</i>-Dimethyl α-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a New Herbicide. 1. Synthesis and Herbicidal Activity of HW02 and Analogues as Novel Inhibitors of Pyruvate Dehydrogenase Complex
  作者：Hong-Wu He、Jun-Lin Yuan、Hao Peng、Ting Chen、Ping Shen、Shu-Qing Wan、Yanjun Li、Hong-Liang Tan、Ya-Hui He、Jun-Bo He、Yan Li

  DOI：10.1021/jf104247w

  日期：2011.5.11

  On the basis of the previous work for optimization of O,O-diethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates, further extensive synthetic modifications were made to the substituents in alkylphosphonate and phenoxy moieties of the title compounds. New O,O-dimethyl alpha-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compounds were studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl alpha-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa , was found to be the most effective compound against broadleaf weeds and showed potential utility as herbicide.
• Synthesis and herbicidal activities of methyl-1-(2,4-dichlorophenoxyacetoxy)alkylphosphonate monosalts
  作者：Hong Wu He、Tao Wang、Jun Lin Yuan

  DOI：10.1016/j.jorganchem.2005.01.061

  日期：2005.5

  A series of 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5 and its corresponding phosphonate monosalts 6 were synthesized as potential herbicide. The phosphonate monosalts can be prepared from 1-(2,4-dichlorophenoxyacetoxy)alkylphosphonic acid dimethyl esters 5, which were synthesized by the condensation of O,O-dimethyl-1-hydroxyalkylphosphonates with dichlorophenoxyacetic chloride. This method provides a simple and efficient procedure for the synthesis of phosphonate derivatives containing sensitive groups to acid, base or water such as carboxylate ester bond; and the herbicidal activity of title compounds was evaluated in a set of experiments in greenhouse. Most of the compounds exhibited notable herbicidal activity. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis and Herbicidal Activities of Sodium Hydrogen 1-(Substituted Phenoxyacetoxy)Alkylphosphonates
  作者：Qingwu Long、Xiaoyan Deng、Yujiao Gao、Huayong Xie、Hao Peng、Hongwu He

  DOI：10.1080/10426507.2012.717147

  日期：2013.7.1

  hydrogen 1-(substituted phenoxyacetoxy) alkylphosphonates was designed and synthesized. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Especially, 8f and 8g showed the best herbicidal activity against rape and amaranth with more than 95% inhibitory rate. Supplemental materials are available

  摘要 设计合成了一系列1-(取代苯氧基乙酰氧基)烷基膦酸氢钠。除草活性试验表明，大多数膦酸盐（8）对阔叶杂草具有优异的芽后除草活性。特别是8f和8g对油菜和苋菜的除草活性最好，抑菌率达95%以上。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要