5-(chlorodifluoromethyl)-3-(7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl)-4-isoxazolecarboxamide | 159693-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 5-(chlorodifluoromethyl)-3-(7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl)-4-isoxazolecarboxamide
• 英文别名: 5-[chloro(difluoro)methyl]-3-(7-fluoro-3-oxo-4H-1,4-benzoxazin-6-yl)-1,2-oxazole-4-carboxamide
• CAS: 159693-97-7
• 化学式: C₁₃H₇ClF₃N₃O₄
• 分子量: 361.664
• InChiKey: RNTUSVAOPBDFBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-溴丙炔 、 5-(chlorodifluoromethyl)-3-(7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl)-4-isoxazolecarboxamide 在 potassium carbonate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 以44%的产率得到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：

  methyl 5-(chlorodifluoromethyl)-3-(2,4-difluoro-5-nitrophenyl)-4-isoxazolecarboxylate 在 盐酸 、 ammonium hydroxide 、 草酰氯 、 水 、 三溴化硼 、 铁粉 、 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 、 丙酮 为溶剂， 反应 6.75h， 生成 5-(chlorodifluoromethyl)-3-(7-fluoro-3,4-dihydro-3-oxo-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