n-butyl 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: n-butyl 2-methoxy-3-trifluoroacetyl-4-quinolylsulfide
• 英文别名: [2-Methoxy-4-(butylthio)-3-quinolyl](trifluoromethyl) ketone；1-(4-butylsulfanyl-2-methoxyquinolin-3-yl)-2,2,2-trifluoroethanone
• 化学式: C₁₆H₁₆F₃NO₂S
• 分子量: 343.37
• InChiKey: CHDQBPDDWCXQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丁硫醇 、 N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine 以 均三甲苯 为溶剂， 反应 120.0h， 以84%的产率得到n-butyl 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

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.