p-(2,2,2-trifluoro-1-trifluoromethylethoxy)nitrobenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-(2,2,2-trifluoro-1-trifluoromethylethoxy)nitrobenzene
• 英文别名: 1-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-4-nitrobenzene
• 化学式: C₉H₅F₆NO₃
• 分子量: 289.134
• InChiKey: VQWAHDWQOWAMDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-(2,2,2-trifluoro-1-trifluoromethylethoxy)nitrobenzene 在 铜 、 氯化铵 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2,6-difluoro-N-(4-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)phenylcarbamoyl)benzamide
  参考文献：
  名称：

  Design and Synthesis of Benzoylphenylureas with Fluorinated Substituents on the Aniline Ring as Insect Growth Regulators

  摘要：

  Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas.

  DOI：

  10.1021/jf104578j
• 作为产物：
  描述：

  对二硝基苯 、 六氟异丙醇 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以34.5%的产率得到p-(2,2,2-trifluoro-1-trifluoromethylethoxy)nitrobenzene
  参考文献：
  名称：

  Design and Synthesis of Benzoylphenylureas with Fluorinated Substituents on the Aniline Ring as Insect Growth Regulators

  摘要：

  Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas.

  DOI：

  10.1021/jf104578j

文献信息

• A Fast Radical Chain Mechanism in the Polyfluoroalkoxylation of Aromatics through NO₂ Group Displacement. Mechanistic and Theoretical Studies
  作者：Ismael Tejero、Imma Huertas、Àngels González-Lafont、José M. Lluch、Jordi Marquet

  DOI：10.1021/jo048354m

  日期：2005.3.1

  chain mechanism operates. This mechanism is elicited by oxidation of a Meisenheimer complex and proceeds through a radical aromatic substitution with the polyfluoroalkoxy or the polyfluoroalkylthio radicals as key intermediates. At low concentrations, entrainment can be achieved with superoxide anion. A rationale for this effect is discussed. Answers to particular questions about the proposed mechanism

  在温和的条件下，在过量的四丁基氟化铵作为碱的存在下，通过适度过量的二硝基苯在DMF中的浓溶液与多氟醇和多氟硫醇的充分彻底反应，可以在芳环中引入多氟烷氧基和多氟烷硫基取代基。机理研究表明，在这些条件下，快速自由基链机制起作用。该机理是由迈森海默配合物的氧化引起的，并通过以多氟烷氧基或多氟烷硫基为主要中间体的自由基芳族取代来进行。在低浓度下，可以用超氧阴离子夹带。讨论了这种效果的原理。通过在B3LYP / 6-31 + G（d，p）级别上进行理论研究，可以找到有关所提出机制的特定问题的答案。具体而言，自由基机理与相应的极性机理（经典S以此方式研究了N Ar反应），结论是在我们的反应条件下（极性非质子溶剂）自由基机理的关键步骤至少与极性反应的效率相同，因此证明了所观察到的动力学优势在发生有效引发的条件下进行链式反应。
• Design and Synthesis of Benzoylphenylureas with Fluorinated Substituents on the Aniline Ring as Insect Growth Regulators
  作者：Ranfeng Sun、Yuxiu Liu、Yonglin Zhang、Lixia Xiong、Qingmin Wang

  DOI：10.1021/jf104578j

  日期：2011.3.23

  Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas.