5-(benzylideneamino)-4-chloro-3-methylisothiazole | 189291-60-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-(benzylideneamino)-4-chloro-3-methylisothiazole
• 英文别名: N-(4-chloro-3-methyl-1,2-thiazol-5-yl)-1-phenylmethanimine
• CAS: 189291-60-9
• 化学式: C₁₁H₉ClN₂S
• 分子量: 236.725
• InChiKey: CWPBYAOBLHSQPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(benzylideneamino)-4-chloro-3-methylisothiazole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 N-benzyl-N-(4-chloro-3-methyl-5-isothiazolyl)-2-{p-[(α,α,α-trifluoro-p-tolyl)oxy]phenyl}acetamide
  参考文献：
  名称：

  N-Alkyl-N-(5-isothiazolyl)- and N-(Alkylisothiazolin-5-ylidene)- phenylacetamides. Synthesis and Biological Activity

  摘要：

  Treatment of 5-amino-4-chloro-3-methylisothiazole (3) with the acid chloride of [p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetic acid (6) afforded the amide N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha, alpha-trifluoro-p-tolyl)oxy]phenyl]acetamide (1), which was substituted with various alkyl groups in an effort to alleviate toxicity toward non-target organisms through a proinsecticide approach. Alkylations of 1 under a variety of reaction conditions afforded two major products which were derived from amide-nitrogen substitution, N-alkyl-N-(4-chloro-3- methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetamides (a), and ring-nitrogen substitution, N-(2-alkyl-4-chloro-3-methyl-3-isothiazolin-5-ylidene)-2-[p- [(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamides(8). Derivatives 7 and 8 were found to exhibit lessened toxicity to trout as well as insects, but, in general, efficacy toward insects was retained to a greater degree. In particular methoxymethyl, ethoxymethyl, ethyl, and ethyl-d(5) substituents demonstrated the best combination of insect efficacy and safening toward trout. Significantly different in vivo efficacies of the N-methyl and N-CD3 analogs suggest that 7 and 8 are proinsecticides requiring activation by dealkylation.

  DOI：

  10.1021/jf960679j
• 作为产物：
  描述：

  苯甲醛 、 5-氨基-4-氯-3-甲基异噻唑 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 以87%的产率得到5-(benzylideneamino)-4-chloro-3-methylisothiazole
  参考文献：
  名称：

  N-Alkyl-N-(5-isothiazolyl)- and N-(Alkylisothiazolin-5-ylidene)- phenylacetamides. Synthesis and Biological Activity

  摘要：

  Treatment of 5-amino-4-chloro-3-methylisothiazole (3) with the acid chloride of [p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetic acid (6) afforded the amide N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha,alpha, alpha-trifluoro-p-tolyl)oxy]phenyl]acetamide (1), which was substituted with various alkyl groups in an effort to alleviate toxicity toward non-target organisms through a proinsecticide approach. Alkylations of 1 under a variety of reaction conditions afforded two major products which were derived from amide-nitrogen substitution, N-alkyl-N-(4-chloro-3- methyl-5-isothiazolyl)-2-[p-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetamides (a), and ring-nitrogen substitution, N-(2-alkyl-4-chloro-3-methyl-3-isothiazolin-5-ylidene)-2-[p- [(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]phenyl] acetamides(8). Derivatives 7 and 8 were found to exhibit lessened toxicity to trout as well as insects, but, in general, efficacy toward insects was retained to a greater degree. In particular methoxymethyl, ethoxymethyl, ethyl, and ethyl-d(5) substituents demonstrated the best combination of insect efficacy and safening toward trout. Significantly different in vivo efficacies of the N-methyl and N-CD3 analogs suggest that 7 and 8 are proinsecticides requiring activation by dealkylation.

  DOI：

  10.1021/jf960679j