5-Amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride | 1041682-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride
• CAS: 1041682-32-9
• 化学式: C₆H₅ClF₃N₃O
• 分子量: 227.573
• InChiKey: XEVKSLQHVQQNNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride 、 4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenylamine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 5-amino-N-(4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

  摘要：

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

  DOI：

  10.1021/jf801774k
• 作为产物：
  描述：

  5-氨基-1-甲基-3-三氟甲基-1H-吡唑-4-羧酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 5-Amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride
  参考文献：
  名称：

  Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

  摘要：

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

  DOI：

  10.1021/jf801774k