4-<4-(aminocarbonyl)-5-(chlorodifluoromethyl)-3-isoxazolyl>-5-fluoro-2-nitrophenoxyacetic acid ethyl ester | 159693-95-5

• 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: 4-<4-(aminocarbonyl)-5-(chlorodifluoromethyl)-3-isoxazolyl>-5-fluoro-2-nitrophenoxyacetic acid ethyl ester
• CAS: 159693-95-5
• 化学式: C₁₅H₁₁ClF₃N₃O₇
• 分子量: 437.716
• InChiKey: BCADCQJHROCKIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  147.79
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-<4-(aminocarbonyl)-5-(chlorodifluoromethyl)-3-isoxazolyl>-5-fluoro-2-nitrophenoxyacetic acid ethyl ester 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 2.0h， 生成 5-(chlorodifluoromethyl)-3-<7-fluoro-3,4-dihydro-3-oxo-1-(2-propynyl)-2H-1,4-benzoxazin-6-yl>-4-isoxazolecarboxamide
  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：

  2,4-difluorobenzaldehyde oxime 在 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 N-氯代丁二酰亚胺 、 草酰氯 、 水 、 硝酸 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.0h， 生成 4-<4-(aminocarbonyl)-5-(chlorodifluoromethyl)-3-isoxazolyl>-5-fluoro-2-nitrophenoxyacetic acid ethyl ester
  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