1-nitro-2-(2,2,2-trifluoroethyl)benzene

• 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: 1-nitro-2-(2,2,2-trifluoroethyl)benzene
• 化学式: C₈H₆F₃NO₂
• 分子量: 205.136
• InChiKey: LMUDYZWHWMEFCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-nitro-2-(2,2,2-trifluoroethyl)benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-(2,2,2-trifluoro-ethyl)-aniline
  参考文献：
  名称：

  A Facile Synthesis of Isomeric C-(2,2,2-Trifluoroethyl)anilines

  摘要：

  Three isomers of C-(2,2,2-trifluoroethyl) aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sulfur tetrafluoride. The obtained 2,2,2-trifluoroethyl-substituted nitrobenzenes were reduced catalytically into the corresponding anilines.

  DOI：

  10.1055/s-0031-1290295
• 作为产物：
  描述：

  2-硝基苯乙酸 在 sulfur tetrafluoride 作用下， 反应 72.0h， 以42%的产率得到1-nitro-2-(2,2,2-trifluoroethyl)benzene
  参考文献：
  名称：

  A Facile Synthesis of Isomeric C-(2,2,2-Trifluoroethyl)anilines

  摘要：

  Three isomers of C-(2,2,2-trifluoroethyl) aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sulfur tetrafluoride. The obtained 2,2,2-trifluoroethyl-substituted nitrobenzenes were reduced catalytically into the corresponding anilines.

  DOI：

  10.1055/s-0031-1290295

文献信息

• Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2‐Trifluoroethyl)arenes
  作者：Zhensheng Zhao、Kevin C. Y. Ma、Claude Y. Legault、Graham K. Murphy

  DOI：10.1002/chem.201902818

  日期：——

  hydrazones of arylaldehydes with Togni's CF3 -benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this

  在氢氧化钾和氟化铯的存在下，芳基醛的azo与Togni的CF3-苯并恶唑酮试剂反应，会引发脱氮加氢三氟甲基化反应，从而生成（2,2,2-三氟乙基）芳烃。这种新颖的反应可耐受许多电子多样性的官能团和取代方式，以及萘基和杂芳基衍生的底物。该方法的优点包括容易大规模获得speed前体，速度和操作简便性，并且不含过渡金属。
• Metal-Free Construction of the C(sp³)–CF₃ Bond: Trifluoromethylation of Hydrazones with Togni’s Reagent under Mild Conditions
  作者：Huiying Zeng、Zhen Luo、Xinlong Han、Chao-Jun Li

  DOI：10.1021/acs.orglett.9b02072

  日期：2019.8.2

  A metal-free trifluoromethylation of hydrazones with Togni’s reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)–CF3 bonds.

  开发了在温和条件下用Togni试剂对进行的无金属三氟甲基化反应。容许各种官能团，包括酯，甲氧基，二甲氧基，硝基，卤素和杂环化合物。这种简单而绿色的策略提供了构建C（sp 3）–CF 3键的实用工具。
• ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND METHOD OF USING THEREOF
  申请人：Merial Inc.

  公开号：EP3428162A1

  公开（公告）日：2019-01-16

  The present invention relates to novel anthelmintic compounds of formula (IA-2) below: wherein Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.

  本发明涉及下式(IA-2)的新型驱虫化合物：其中Y和Z独立地为双环碳环或双环杂环基团，或Y或Z之一为双环碳环或双环杂环基团，Y或Z的另一个为烷基、烯基、炔基、环烷基、苯基、杂环基或杂芳基。本发明还提供了包含本发明抗蠕虫化合物的兽用组合物，以及它们在治疗和预防动物寄生虫感染方面的用途。
• The reactions of copper-dibromodifluoromethane-amide systems with alcohols
  作者：James H. Clark、Martin A. McClinton、Robert J. Blade

  DOI：10.1016/s0022-1139(00)82418-5

  日期：1992.11

  1,1,1-Trifluoro-2-arylethanes can be prepared by the trifluoromethyldehydroxylation of benzYl alcohols using the copper-dibromodifluoromethane-amide reaction system, although the yields are low. The mechanism of the reaction may involve chelation of the substrate to copper so that alpha-substituted benzyl alcohols and most other alcohols are unreactive.
• Cu-Mediated Chemoselective Trifluoromethylation of Benzyl Bromides Using Shelf-Stable Electrophilic Trifluoromethylating Reagents
  作者：Hiroyuki Kawai、Tatsuya Furukawa、Yoshinori Nomura、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/ol201205t

  日期：2011.7.15

  Copper-mediated chemoselective trifluoromethylation at the benzylic :position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.