N-(2-Bromo-4-nitro-phenyl)-2,2,2-trifluoro-acetamide

• 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: N-(2-Bromo-4-nitro-phenyl)-2,2,2-trifluoro-acetamide
• 英文别名: N-(2-bromo-4-nitrophenyl)-2,2,2-trifluoroacetamide
• 化学式: C₈H₄BrF₃N₂O₃
• 分子量: 313.031
• InChiKey: SOSOLXKUOMUSHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  哌喃 、 N-(2-Bromo-4-nitro-phenyl)-2,2,2-trifluoro-acetamide 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以69%的产率得到5-nitro-2-((tetrahydro-2H-pyran-2-yloxy)methyl)indole
  参考文献：
  名称：

  Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides

  摘要：

  Cross-coupling of 1-alkynes with vinyl iodides occurs at 80 degrees C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 degrees C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables the reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.

  DOI：

  10.1021/jo070547x

文献信息

• Synthesis of indoles and quinolones by sequential Wittig and Heck reactions
  作者：Elliot J. Latham、Stephen P. Stanforth

  DOI：10.1039/cc9960002253

  日期：——

  N-Trifluoroacetylanilines 6 and 7 undergo a Wittig reaction with phosphorane 2 (R = Et) giving enamine derivatives 9 and 10 respectively which are precursors to indoles 4 and quinolones 5.

  N-三氟乙酰苯胺 6 和 7 与磷烷 2（R = Et）发生维蒂希反应，分别生成烯胺衍生物 9 和 10，它们是吲哚类化合物 4 和喹诺酮类化合物 5 的前体。
• Latham, Elliot J.; Stanforth, Stephen P., Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2059 - 2063
  作者：Latham, Elliot J.、Stanforth, Stephen P.

  DOI：——

  日期：——