N,N-dimethyl-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: N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine
• 英文别名: 4-dimethylamino-2-methoxy-3-trifluoroacetylquinoline；2-Methoxy-3-(trifluoroacetyl)-4-(dimethylamino)quinoline；1-[4-(dimethylamino)-2-methoxyquinolin-3-yl]-2,2,2-trifluoroethanone
• 化学式: C₁₄H₁₃F₃N₂O₂
• 分子量: 298.265
• InChiKey: HWFSGQISZFYFLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以100%的产率得到4-methoxy-3-(trifluoromethyl)-1H-pyrazolo[4,3-c]quinoline
  参考文献：
  名称：

  Facile Syntheses of Fluorine-Containing 4-Methoxypyrazolo[4,3-c]quinolines and 6-Methoxy-1,4-diazepino[6,5-c]quinolines

  摘要：

  N,N-Dimethy1-2-methoxy-3-trifluoroacety1-4-quinolylamine underwent chemoselective aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding novel fluorine-containing 4-methoxy-1H-and 2H-pyrazolo[4,3-c]quinolines in good to high yields. Furthermore, the use of 1,2-ethylenediamine and 1,2-phenylenediamines gave the corresponding fluorine-containing 6-methoxy-1,4-diazepino[6,5-c]quinoline derivatives in good yields.

  DOI：

  10.3987/com-16-13420
• 作为产物：
  描述：

  2-methoxy-3-trifluoroacetyl-4-quinolylamine 、 碘甲烷 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以67%的产率得到N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine
  参考文献：
  名称：

  4-二甲氨基-2-甲氧基-3-三氟乙酰喹啉的高化学选择性亲核取代反应高效合成含氟二苯并[b,h][1,6]萘啶和硫代色素[3,2-c]喹啉

  摘要：

  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.

  DOI：

  10.3987/com-16-s(s)23

文献信息

• Unexpected Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline with Various Nucleophiles
  作者：Etsuji Okada、Mizuki Hatakenaka、Keisuke Iwakuni

  DOI：10.3987/com-15-s(t)54

  日期：——

  Aromatic nucleophilic substitution reaction of 4-dimethylamino-2-methoxy-3-trifluoroacetylquinoline with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively to give the corresponding Me2N-Nu exchanged products, 2-methoxy-3-trifluoroacetyl-4-quinolylamines, sulfides, and ethers without any formation of MeO-Nu exchanged products in spite of the common knowledge that alkoxy group is the better leaving group than amino group.
• 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 Syntheses of Fluorine-Containing 4-Methoxypyrazolo[4,3-c]quinolines and 6-Methoxy-1,4-diazepino[6,5-c]quinolines
  作者：Etsuji Okada、Mizuki Hatakenaka、Satoru Adachi

  DOI：10.3987/com-16-13420

  日期：——

  N,N-Dimethy1-2-methoxy-3-trifluoroacety1-4-quinolylamine underwent chemoselective aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding novel fluorine-containing 4-methoxy-1H-and 2H-pyrazolo[4,3-c]quinolines in good to high yields. Furthermore, the use of 1,2-ethylenediamine and 1,2-phenylenediamines gave the corresponding fluorine-containing 6-methoxy-1,4-diazepino[6,5-c]quinoline derivatives in good yields.