7,8-dimethoxy-2,5-dihydropyrido[4,3-b]indol-1-one | 267666-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7,8-dimethoxy-2,5-dihydropyrido[4,3-b]indol-1-one
• CAS: 267666-62-6
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: SXTQQAQWCRIGGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxy-2,5-dihydropyrido[4,3-b]indol-1-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(3-Dimethylamino-propyl)-7,8-dimethoxy-2,5-dihydro-pyrido[4,3-b]indol-1-one
  参考文献：
  名称：

  Lewis Acid-Directed Cyclocondensation of Piperidone Enol Ethers with 2-Methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:  A New Regioselective Synthesis of Oxygenated Carbolines

  摘要：

  Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.

  DOI：

  10.1021/jo9916176
• 作为产物：
  描述：

  1-(苯基磺酰基)哌啶-4-酮 在 titanium(IV) isopropylate 、 三氯化铝 、 selenium(IV) oxide 、 sodium acetate 、 乙酸酐 、 四氯化钛 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 145.5h， 生成 7,8-dimethoxy-2,5-dihydropyrido[4,3-b]indol-1-one
  参考文献：
  名称：

  Lewis Acid-Directed Cyclocondensation of Piperidone Enol Ethers with 2-Methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:  A New Regioselective Synthesis of Oxygenated Carbolines

  摘要：

  Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.

  DOI：

  10.1021/jo9916176

文献信息

• Lewis Acid-Directed Cyclocondensation of Piperidone Enol Ethers with 2-Methoxy-4-(<i>N</i>-phenylsulfonyl)-1,4-benzoquinoneimine:  A New Regioselective Synthesis of Oxygenated Carbolines
  作者：Thomas A. Engler、Jutta Wanner

  DOI：10.1021/jo9916176

  日期：2000.4.1

  Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.