1,2-Dihydro-8-methoxy-1-methyl-2-oxopyrrolo<4,3,2-de>quinoline | 157035-64-8

• 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: 1,2-Dihydro-8-methoxy-1-methyl-2-oxopyrrolo<4,3,2-de>quinoline
• 英文别名: 11-Methoxy-2-methyl-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-3-one
• CAS: 157035-64-8
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: VTIFJMRHGUBHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-Dihydro-8-methoxy-1-methyl-2-oxopyrrolo<4,3,2-de>quinoline 在 sodium tetrahydroborate 、 水 、 氧气 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,2a,3,4,5-Hexahydro-2a-hydroxy-8-methoxy-1,5-dimethyl-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 盐酸 、 selenium(IV) oxide 、 硝酸 、 ammonium formate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.75h， 生成 1,2-Dihydro-8-methoxy-1-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

文献信息

• Transformation of 2,2-dioxoisothiazolo[5,4,3-d,e]quinolines to pyrrolo[4,3,2-d,e]quinolin-2(1H)-ones
  作者：Zbigniew Wróbel

  DOI：10.1016/s0040-4039(01)01024-3

  日期：2001.8

  The sulfonamide group in 1H-1-alkyl-8-X-2,2-dioxoisothiazolo[5,4,3-d,e]quinolines 2 undergoes substitution with cyanide anion giving after hydrolysis pyrrolo[4,3,2-d,e]quinolin-2(1H)-ones 3. (C) 2001 Elsevier Science Ltd. Ail rights reserved.
• 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.