5-(Acetylamino)-6-methoxy-4-methylquinoline | 157035-52-4

• 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: 5-(Acetylamino)-6-methoxy-4-methylquinoline
• 英文别名: N-(6-methoxy-4-methylquinolin-5-yl)acetamide
• CAS: 157035-52-4
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: VUQMMGYEXLFJCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(Acetylamino)-6-methoxy-4-methylquinoline 在 盐酸 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 水 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 62.08h， 生成 1,2,2a,3,4,5-Hexahydro-2a-hydroxy-8-methoxy-5-methyl-2-oxopyrrolo<4,3,2-de>quinoline
  参考文献：
  名称：

  Synthesis of Some Pyrrolo[4,3,2-de]quinolines

  摘要：

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.

  DOI：

  10.1021/jo00095a037
• 作为产物：
  描述：

  6-甲氧基-4-甲基喹啉水合物 在 palladium on activated charcoal 硝酸 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 5-(Acetylamino)-6-methoxy-4-methylquinoline
  参考文献：
  名称：

  Synthesis of Some Pyrrolo[4,3,2-de]quinolines

  摘要：

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.

  DOI：

  10.1021/jo00095a037

文献信息

• Synthesis of Some Pyrrolo[4,3,2-de]quinolines
  作者：Piotr Balczewski、John A. Joule、Carlos Estevez、Mercedes Alvarez

  DOI：10.1021/jo00095a037

  日期：1994.8

  The selenium dioxide oxidation of the methyl group in 5-acetamido-6-methoxy-4-methylquinoline produced 1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinoline, 8b. Halogenation and nitration of 8b gave and 6-substituted derivatives 8c-e. 6-Halo-1,2-dihydro-8-methoxy-2-oxopyrrolo[4,3,2-de]quinolines were O-demethylated, giving phenols 8g and 8h. Reaction of 8b, and its N-methyl derivative 8i, with iodomethane resulted in quaternization of the quinoline ring nitrogen; borohydride reduction of the salts thus produced, and then aerial oxidation, led to dioxindoles 12a,b and 13a,b. Lithium aluminum hydride reduction of 12a produced indole 10b.