2-methoxy-3-trifluoroacetyl-4-quinolylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methoxy-3-trifluoroacetyl-4-quinolylamine
• 英文别名: 2-Methoxy-3-(trifluoroacetyl)-4-aminoquinoline；1-(4-amino-2-methoxyquinolin-3-yl)-2,2,2-trifluoroethanone
• 化学式: C₁₂H₉F₃N₂O₂
• 分子量: 270.211
• InChiKey: XDQNFSXVUXHQLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-trifluoroacetyl-4-quinolylamine 在 ammonium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 49.0h， 生成 5-methoxy-2-(p-tolyl)-4-(trifluoromethyl)pyrimido[5,4-c]quinoline
  参考文献：
  名称：

  2-Methoxy-3-trifluoroacetyl-4-quinolylamine 与醛酮缩合反应简便合成含氟嘧啶并[5,4-c]喹啉和苯并[h][1,6]萘啶

  摘要：

  2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.

  DOI：

  10.3987/com-16-13595
• 作为产物：
  描述：

  1,1,1-trifluoro-4,4-dimethoxybut-3-en-2-one 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 18.08h， 生成 2-methoxy-3-trifluoroacetyl-4-quinolylamine
  参考文献：
  名称：

  2-Methoxy-3-trifluoroacetyl-4-quinolylamine 与醛酮缩合反应简便合成含氟嘧啶并[5,4-c]喹啉和苯并[h][1,6]萘啶

  摘要：

  2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.

  DOI：

  10.3987/com-16-13595

文献信息

• Efficient Synthesis of Fluorine-Containing Dibenzo[b,h][1,6]naphthyridines and Thiochromeno[3,2-c]quinolines Using Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline
  作者：Etsuji Okada、Mizuki Hatakenaka、Yoshinori Takezawa、Keisuke Iwakuni

  DOI：10.3987/com-16-s(s)23

  日期：——

  Aromatic nucleophilic substitution reaction of N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively at the 4-position to give the corresponding Me2N-Nu exchanged products. Novel fluorine-containing 6-methoxydibenzo[b,h][1,6]naphthyridines (11) and 6-methoxythiochromeno[3,2-c]quinolines (12) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of thus obtained N-aryl-2-methoxy-3-trifluoroacetyl-4-quinolylamines (8) and aryl 2-methoxy-3-trifluoroacetyl-4-quinolyl sulfides (9), respectively.
• Facile and Convenient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reaction of 2-Methoxy-3-trifluoroacetyl-4-quinolylamine with Aldehydes and Ketones
  作者：Etsuji Okada、Mizuki Hatakenaka

  DOI：10.3987/com-16-13595

  日期：——

  2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.