(1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethyl-N-[2-(trifluoromethyl)phenyl]cyclopropane-1-carboxamide

• 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: (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethyl-N-[2-(trifluoromethyl)phenyl]cyclopropane-1-carboxamide
• 化学式: C₁₅H₁₄Cl₂F₃NO
• 分子量: 352.183
• InChiKey: ODILXTQDORQEFB-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-cis-(1S,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethyl-N-[2-(trifluoromethyl)phenyl]cyclopropane-1-carboxamide
  参考文献：
  名称：

  Synthesis and Larvicidal Properties of Some Cyclopropylcarboxamides Related to cis-Permethrin

  摘要：

  Twenty-seven carboxamide derivatives of (+/-)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (permethrin acid) have been synthesized and evaluated in the laboratory against mosquito larvae (Aedes aegypti). These cis-cyclopropylcarboxamides, with N-(substituted)phenyl, N-(substituted)phenylmethyl, N-(substituted)phenylethyl, N-phenylpropyl, and N-phenylbutyl groups, were synthesized from the acid chloride of permethrin acid and various arylamines in methylene chloride. The samples were characterized by C-13 NMR spectroscopy and mass spectrometry. Secondary amides with electron-donating (e.g., methoxy) and electron-withdrawing (e.g., trifluoromethyl) substituents on the phenyl ring as well as nine tertiary amides were investigated. 3-(2,2-Dichloroethenyl)-2,2-dimethyl-N-(3-phenoxyphenyl)methylcyclopropanecarboxamide was the most active experimental compound and was 25 times less potent than (+/-)-cis-permethrin. Cyclopropylcarboxamides of the N-(substituted)phenyl, N-(substituted)phenylethyl, and N-phenylpropyl types were essentially inactive in the larvicidal tests.

  DOI：

  10.1021/jf9705375