5-(chlorodifluoromethyl)-3-(4-chlorophenyl)-4-isoxazolecarboxylic acid | 159693-77-3

• 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: 5-(chlorodifluoromethyl)-3-(4-chlorophenyl)-4-isoxazolecarboxylic acid
• 英文别名: 5-[Chloro(difluoro)methyl]-3-(4-chlorophenyl)-1,2-oxazole-4-carboxylic acid；5-[chloro(difluoro)methyl]-3-(4-chlorophenyl)-1,2-oxazole-4-carboxylic acid
• CAS: 159693-77-3
• 化学式: C₁₁H₅Cl₂F₂NO₃
• 分子量: 308.068
• InChiKey: IKUJNIIODZFUSS-UHFFFAOYSA-N

物化性质

• 沸点：
  420.392±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.583±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(chlorodifluoromethyl)-3-(4-chlorophenyl)-4-isoxazolecarboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到5-(chlorodifluoromethyl)-3-(4-chlorophenyl)-4-isoxazolecarbonyl chloride
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives

  摘要：

  A series of unique 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides have been prepared which exhibit, in both greenhouse and field studies, significant preemergent and postemergent herbicidal activity in the grams per hectare range against broadleaf and narrowleaf weeds. The key step in the formation of the fully substituted isoxazole ring 2 is 1,3 dipolar cycloaddition of a haloalkyl-substituted acetylenic ester and a nitrile oxide intermediate. The 3-aryl-5-(halo alkyl)-4-isoxazolecarboxylate esters 2 are converted to isoxazole-4-carboxamide herbicides 5 and 6, secondary amides 7, and amino acid derivatives 8. Greatest activity was observed with compounds having a combination of three substituents: a substituted phenyl ring in the 3-position, a primary or secondary carboxamide in the 4-position, and a difluorochloromethyl group in the, 5-position of the isoxazole ring.

  DOI：

  10.1021/jf00049a040
• 作为产物：
  描述：

  Alpha,4-二氯苯甲醛肟 在 盐酸 、 sodium hydroxide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 72.25h， 生成 5-(chlorodifluoromethyl)-3-(4-chlorophenyl)-4-isoxazolecarboxylic acid
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives

  摘要：

  A series of unique 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides have been prepared which exhibit, in both greenhouse and field studies, significant preemergent and postemergent herbicidal activity in the grams per hectare range against broadleaf and narrowleaf weeds. The key step in the formation of the fully substituted isoxazole ring 2 is 1,3 dipolar cycloaddition of a haloalkyl-substituted acetylenic ester and a nitrile oxide intermediate. The 3-aryl-5-(halo alkyl)-4-isoxazolecarboxylate esters 2 are converted to isoxazole-4-carboxamide herbicides 5 and 6, secondary amides 7, and amino acid derivatives 8. Greatest activity was observed with compounds having a combination of three substituents: a substituted phenyl ring in the 3-position, a primary or secondary carboxamide in the 4-position, and a difluorochloromethyl group in the, 5-position of the isoxazole ring.

  DOI：

  10.1021/jf00049a040