dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate | 920750-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate
• 英文别名: Dimethyl 3-(chloromethyl)-1,2-oxazole-4,5-dicarboxylate；dimethyl 3-(chloromethyl)-1,2-oxazole-4,5-dicarboxylate
• CAS: 920750-30-7
• 化学式: C₈H₈ClNO₅
• 分子量: 233.608
• InChiKey: UJHFPUMTDRVROU-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±42.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate 、 3-甲氧基苯硫酚 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 dimethyl 3-(((3-methoxyphenyl)thio)methyl)isoxazole-4,5-dicarboxylate
  参考文献：
  名称：

  3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity

  摘要：

  A collection of 91 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides was prepared starting from dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate. The thioether moieties in these compounds were subsequently oxidized to give the corresponding 3-(arylsulfonylmethyl)isoxazole-4,5-dicarboxamides. By carefully controlling stoichiometry and reaction conditions, the C4 and C5 carbomethoxy groups could be differentially derivatized to carboxamides. A total of 182 trisubstituted isoxazoles are reported and deposited in the National Institutes of Health Molecular Repository; an 80 compound subset was evaluated for insecticidal activity.

  DOI：

  10.1021/jf901512t
• 作为产物：
  描述：

  1-氯乙醛肟 、 丁炔二酸二甲酯 在 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate
  参考文献：
  名称：

  3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity

  摘要：

  A collection of 91 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides was prepared starting from dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate. The thioether moieties in these compounds were subsequently oxidized to give the corresponding 3-(arylsulfonylmethyl)isoxazole-4,5-dicarboxamides. By carefully controlling stoichiometry and reaction conditions, the C4 and C5 carbomethoxy groups could be differentially derivatized to carboxamides. A total of 182 trisubstituted isoxazoles are reported and deposited in the National Institutes of Health Molecular Repository; an 80 compound subset was evaluated for insecticidal activity.

  DOI：

  10.1021/jf901512t