N-(5-(difluoromethoxy)-2-hydroxyphenyl)-2,2,2-trifluoroacetamide | 1638101-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(5-(difluoromethoxy)-2-hydroxyphenyl)-2,2,2-trifluoroacetamide
• CAS: 1638101-82-2
• 化学式: C₉H₆F₅NO₃
• 分子量: 271.144
• InChiKey: SZOCJSJTUOLPQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  diethyl 2-(((3-(difluoromethoxy)phenyl)amino)methylene)malonate 、 三氟乙酸 在 Oxone 作用下， 以 1,4-二氧六环 为溶剂， 以64%的产率得到N-(5-(difluoromethoxy)-2-hydroxyphenyl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Direct C–N bond cleavage of N-vinyl or N-allyl arylamines: a metal-free strategy for N-devinylation and N-deallylation

  摘要：

  A simple and convenient N-devinylation and N-deallylation strategy for N-vinyl and N-allyl arylamines in the presence of TFA/oxone is presented with the formation of selective ortho-hydroxylated and N-triflu-oroacylated arylamine product in good yields. This method is important for protection/deprotection of arylamines in organic synthesis and useful as a medicinal chemistry tool at late stage modifications in drug discovery programs. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.042

文献信息

• CH Oxygenation and<i>N</i>-Trifluoroacylation of Arylamines Under Metal-Free Conditions: A Convenient Approach to 2-Aminophenols and<i>N</i>-Trifluoroacyl-<i>ortho</i>-aminophenols
  作者：Vunnam Venkateswarlu、K. A. Aravinda Kumar、Shilpi Balgotra、G. Lakshma Reddy、M. Srinivas、Ram A. Vishwakarma、Sanghapal D. Sawant

  DOI：10.1002/chem.201402411

  日期：2014.5.26

  Direct ortho‐hydroxylation through CH oxygenation and N‐trifluoroacylation of anilines was achieved in a single step under metal‐free conditions by using a combination of TFA and oxone. The method allowed the formation of functionalised amino phenolic compounds such as ortho‐hydroxy‐N‐trifluoroacetanilides in good yields with broad substrate scope.

  通过在无金属条件下，通过使用TFA和过硫酸氢钾的组合，一步实现苯胺的CH 3 H氧化和N-三氟酰化直接邻羟基化。该方法可以形成功能化的氨基酚类化合物，例如邻-羟基-N-三氟乙酰苯胺，收率高，具有广泛的底物范围。
• Metal-Free Chemoselective ortho-C(sp2)–F Bond Hydroxylation and N-Trifluoroacylation of Fluoroarylamines for Domino Synthesis of 2-(N-Trifluoroacyl)aminophenols
  作者：Sanghapal Sawant、Vunnam Venkateswarlu、Shilpi Balgotra、K. Aravinda Kumar、Ram Vishwakarma

  DOI：10.1055/s-0034-1379905

  日期：——

  A novel chemoselective reaction for the formation of C-O bonds by C(sp(2))-F bond cleavage and concomitant N-trifluoroacylation of fluoroanilines using trifluoroacetic acid and Oxone((R)) is presented. This domino reaction gives o-hydroxy-N-trifluoroacetanilides in good yields under metal-free conditions in a single step. Selective ortho-directed monohydroxylation and N-trifluoroacylation of 2- and 6-fluoro- or 2,6-difluoro-substituted anilines takes place in this transformation.