5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-benzoic acid ethyl ester | 182288-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-benzoic acid ethyl ester
• 英文别名: Ethyl 5-(4-chloro-1-methyl-5-methylsulfanylpyrazol-3-yl)oxy-2-(trifluoromethyl)benzoate
• CAS: 182288-96-6
• 化学式: C₁₅H₁₄ClF₃N₂O₃S
• 分子量: 394.802
• InChiKey: LCTAQNVBKPWUQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-benzoic acid ethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到5-(4-Chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-benzoic acid ethyl ester
  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-chloro-3-hydroxy-1-methyl-5-methylthiopyrazole 在 亚硝酸特丁酯 、 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-benzoic acid ethyl ester
  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