9-benzenesulfonyl-6,7-dimethoxy-2-(2-nitrobenzenesulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline | 267666-41-1

• 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: 9-benzenesulfonyl-6,7-dimethoxy-2-(2-nitrobenzenesulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 9-(benzenesulfonyl)-6,7-dimethoxy-2-(2-nitrophenyl)sulfonyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 267666-41-1
• 化学式: C₂₅H₂₃N₃O₈S₂
• 分子量: 557.605
• InChiKey: WWCUTVVFDLNTIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-benzenesulfonyl-6,7-dimethoxy-2-(2-nitrobenzenesulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline 在 lithium hydroxide 、 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以60%的产率得到9-Benzenesulfonyl-6,7-dimethoxy-2,3,4,9-tetrahydro-1H-β-carboline
  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-(2-Nitrophenyl)sulfonylpiperidin-3-one 在 三氯化铝 、 四丁基碘化铵 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 44.5h， 生成 9-benzenesulfonyl-6,7-dimethoxy-2-(2-nitrobenzenesulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
  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.