Acetic acid [5-(4-chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-phenylcarbamoyl]-methyl ester | 182289-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid [5-(4-chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-phenylcarbamoyl]-methyl ester
• 英文别名: [2-[5-(4-Chloro-1-methyl-5-methylsulfonylpyrazol-3-yl)oxy-2-(trifluoromethyl)anilino]-2-oxoethyl] acetate
• CAS: 182289-49-2
• 化学式: C₁₆H₁₅ClF₃N₃O₆S
• 分子量: 469.826
• InChiKey: GGQGLERPZZDWLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid [5-(4-chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-phenylcarbamoyl]-methyl ester 在 水 作用下， 以31%的产率得到N-[5-(4-Chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-phenyl]-2-hydroxy-acetamide
  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-1-methyl-5-(methylthio)-3-[3-nitro-4-(trifluoromethyl)phenoxy]pyrazole 在 铁粉 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.83h， 生成 Acetic acid [5-(4-chloro-5-methanesulfonyl-1-methyl-1H-pyrazol-3-yloxy)-2-trifluoromethyl-phenylcarbamoyl]-methyl 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