1-Methyl-3-(3-nitro-4-trifluoromethyl-phenoxy)-5-trifluoromethyl-1H-pyrazole | 182289-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Methyl-3-(3-nitro-4-trifluoromethyl-phenoxy)-5-trifluoromethyl-1H-pyrazole
• 英文别名: 1-Methyl-3-[3-nitro-4-(trifluoromethyl)phenoxy]-5-(trifluoromethyl)pyrazole
• CAS: 182289-74-3
• 化学式: C₁₂H₇F₆N₃O₃
• 分子量: 355.196
• InChiKey: BHLHMIMLSVEAFC-UHFFFAOYSA-N

物化性质

• 沸点：
  363.786±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.590±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-Methyl-3-(3-nitro-4-trifluoromethyl-phenoxy)-5-trifluoromethyl-1H-pyrazole 在 1,3-二氯-5,5-二甲基海因 作用下， 以 乙腈 为溶剂， 以63%的产率得到4-Chloro-1-methyl-3-(3-nitro-4-trifluoromethyl-phenoxy)-5-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis and QSAR of Herbicidal 3-Pyrazolyl α,α,α-Trifluorotolyl Ethers

  摘要：

  Pyrazole nitrophenyl ethers (PPEs) were recently identified as a novel class of chemistry exerting herbicidal effects by inhibition of protoporphyrinogen IX oxidase. This area of chemistry has been extended to include herbicidal pyrazolyl fluorotolyl ethers. In these compounds, a trifluoromethyl group substitutes for the 4'-nitro group found in the original herbicides and in ''classical'' nitrodiphenyl ether hebicides. Fluoroanisole pyrazole ethers, in which a trifluoromethoxy group replaces the nitro group of diphenyl ether herbicides, are also described. The shift from 4'-nitro to 4'-trifluoromethyl substitution, which is conservative in terms of electrostatics, produced a novel class of herbicide with substantial pre-emergent activity on narrowleaf weed species. Quantitative structure/activity relationships obtained with respect to substitution on the pyrazole ring and at the 3'-position of the fluorotolyl moiety can be summarized effectively by comparative molecular field analysis. In general, 5-methanesulfonyl fluorotoluidide ethers were found to be most active.

  DOI：

  10.1021/jf9601978
• 作为产物：
  描述：

  4-氟-3-硝基三氟甲苯 在 palladium on activated charcoal 盐酸 、 亚硝酸特丁酯 、 硫酸 、 氢气 、 硝酸 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 1-Methyl-3-(3-nitro-4-trifluoromethyl-phenoxy)-5-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis and QSAR of Herbicidal 3-Pyrazolyl α,α,α-Trifluorotolyl Ethers

  摘要：

  Pyrazole nitrophenyl ethers (PPEs) were recently identified as a novel class of chemistry exerting herbicidal effects by inhibition of protoporphyrinogen IX oxidase. This area of chemistry has been extended to include herbicidal pyrazolyl fluorotolyl ethers. In these compounds, a trifluoromethyl group substitutes for the 4'-nitro group found in the original herbicides and in ''classical'' nitrodiphenyl ether hebicides. Fluoroanisole pyrazole ethers, in which a trifluoromethoxy group replaces the nitro group of diphenyl ether herbicides, are also described. The shift from 4'-nitro to 4'-trifluoromethyl substitution, which is conservative in terms of electrostatics, produced a novel class of herbicide with substantial pre-emergent activity on narrowleaf weed species. Quantitative structure/activity relationships obtained with respect to substitution on the pyrazole ring and at the 3'-position of the fluorotolyl moiety can be summarized effectively by comparative molecular field analysis. In general, 5-methanesulfonyl fluorotoluidide ethers were found to be most active.

  DOI：

  10.1021/jf9601978