4-methoxyphenyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide

• 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: 4-methoxyphenyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide
• 英文别名: p-anisyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide；1-[2-Methoxy-4-[(4-methoxyphenyl)thio]quinoline-3-yl]-2,2,2-trifluoroethanone；2,2,2-trifluoro-1-[2-methoxy-4-(4-methoxyphenyl)sulfanylquinolin-3-yl]ethanone
• 化学式: C₁₉H₁₄F₃NO₃S
• 分子量: 393.386
• InChiKey: DMHMKWJNOMUBER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以97%的产率得到6,9-dimethoxy-7-(trifluoromethyl)-7H-thiochromeno[3,2-c]quinolin-7-ol
  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
• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine 以 对二甲苯 为溶剂， 反应 72.0h， 以79%的产率得到4-methoxyphenyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide
  参考文献：
  名称：

  Unexpected Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline with Various Nucleophiles

  摘要：

  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.

  DOI：

  10.3987/com-15-s(t)54