(E)-N-(4-chloro-3-methyl-5-isothiazolyl)-β-(ethylamino)-p-[(α,α,α-trifluoro-p-tolyl)oxy]atropamide

• 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: (E)-N-(4-chloro-3-methyl-5-isothiazolyl)-β-(ethylamino)-p-[(α,α,α-trifluoro-p-tolyl)oxy]atropamide
• 英文别名: (E)-N-(4-chloro-3-methyl-1,2-thiazol-5-yl)-3-(ethylamino)-2-[4-[4-(trifluoromethyl)phenoxy]phenyl]prop-2-enamide
• 化学式: C₂₂H₁₉ClF₃N₃O₂S
• 分子量: 481.926
• InChiKey: BXYALJUQMUEOAX-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl]acetamide 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 33.0h， 生成 (E)-N-(4-chloro-3-methyl-5-isothiazolyl)-β-(ethylamino)-p-[(α,α,α-trifluoro-p-tolyl)oxy]atropamide
  参考文献：
  名称：

  Methylene Group Modifications of the N-(Isothiazol-5-yl)phenylacetamides. Synthesis and Insecticidal Activity

  摘要：

  It has been shown that oxidation at the ct-carbon of N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamide (1) is conveniently brought about using dimethylformamide dimethylacetal to give N-(4-chloro-3-methyl-5-isothiazolyl)-beta-(dimethylamino)-p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]atropamide (2), which has served as a common starting point for a variety of functional group transformations. These transformations were found to proceed in moderate to good yields to give derivatives of 1 that retained much of the efficacy associated with the parent amide and have allowed for an expansion of the SAR to be developed. Examples of enamines, enols, enol (thio)ethers, oximes, and hydrazones were prepared. In particular, the enamines derived from law molecular weight amines and amino acids were most active as broad-spectrum insecticides and were found to be even more active than 1 on root-knot nematode.

  DOI：

  10.1021/jf990095s

文献信息

• Methylene Group Modifications of the <i>N</i>-(Isothiazol-5-yl)phenylacetamides. Synthesis and Insecticidal Activity
  作者：Jack G. Samaritoni、Jon M. Babcock、Michelle L. Schlenz、George W. Johnson

  DOI：10.1021/jf990095s

  日期：1999.8.1

  It has been shown that oxidation at the ct-carbon of N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamide (1) is conveniently brought about using dimethylformamide dimethylacetal to give N-(4-chloro-3-methyl-5-isothiazolyl)-beta-(dimethylamino)-p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]atropamide (2), which has served as a common starting point for a variety of functional group transformations. These transformations were found to proceed in moderate to good yields to give derivatives of 1 that retained much of the efficacy associated with the parent amide and have allowed for an expansion of the SAR to be developed. Examples of enamines, enols, enol (thio)ethers, oximes, and hydrazones were prepared. In particular, the enamines derived from law molecular weight amines and amino acids were most active as broad-spectrum insecticides and were found to be even more active than 1 on root-knot nematode.