7-Fluoro-6-(4-oxo-7-prop-2-enylpyrazolo[3,4-d]triazin-3-yl)-4-prop-2-ynyl-1,4-benzoxazin-3-one | 1041682-00-1

• 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: 7-Fluoro-6-(4-oxo-7-prop-2-enylpyrazolo[3,4-d]triazin-3-yl)-4-prop-2-ynyl-1,4-benzoxazin-3-one
• CAS: 1041682-00-1
• 化学式: C₁₈H₁₃FN₆O₃
• 分子量: 380.338
• InChiKey: XLVPSZSHQJIJET-UHFFFAOYSA-N

物化性质

• 沸点：
  681.3±65.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氨基-4-乙氧羰基吡唑 、 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以24.3%的产率得到7-Fluoro-6-(4-oxo-6-prop-2-enylpyrazolo[3,4-d]triazin-3-yl)-4-prop-2-ynyl-1,4-benzoxazin-3-one
  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

文献信息

• Novel Protoporphyrinogen Oxidase Inhibitors: 3<i>H</i>-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives
  作者：Hua-bin Li、You-quan Zhu、Xiao-wei Song、Fang-zhong Hu、Bin Liu、Yong-hong Li、Zi-xia Niu、Pei Liu、Zhi-hong Wang、Hai-bin Song、Xiao-mao Zou、Hua-zheng Yang

  DOI：10.1021/jf801774k

  日期：2008.10.22

  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.