2,5-bis-benzenesulfonyl-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 196882-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis-benzenesulfonyl-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 2,5-bis(benzenesulfonyl)-7-methoxy-3,4-dihydro-1H-pyrido[4,3-b]indol-8-ol
• CAS: 196882-99-2
• 化学式: C₂₄H₂₂N₂O₆S₂
• 分子量: 498.58
• InChiKey: RWVHVFALECGAAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-bis-benzenesulfonyl-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium acetate 、 乙酸酐 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 68.5h， 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
• 作为产物：
  描述：

  1-(苯基磺酰基)哌啶-4-酮 在 titanium(IV) isopropylate 、 三氯化铝 、 四氯化钛 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 2,5-bis-benzenesulfonyl-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  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 Reactions of Benzoquinone Mono-/Bis-imines: Application to Syntheses of Substituted β- and γ-Tetrahydrocarbolines
  作者：Thomas A Engler、Jutta Wanner

  DOI：10.1016/s0040-4039(97)01391-9

  日期：1997.9

  Ti(IV)-promoted reactions of N-phenylsulfonyl-3- and 4-piperidone enol ethers with 2-alkoxy-4-(N-phenylsulfonyl)imino-1,4-benzoquinone afford 8-alkoxy-7-hydroxy-tetrahydrocarbolines. However, reactions promoted by BF3 produce substituted benzofurans. Ti(IV)- or BF3-promoted reactions of 2-alkoxy-1-(N-benzoyl)-4-(N-phenylsulfonyl)-1,4-benzoquinone bisimines also afford substituted tetrahydrocarboline

  N-苯基磺酰基-3-和4-哌啶酮烯醇醚与2-烷氧基-4-（N-苯基磺酰基）亚氨基-1,4-苯醌的Ti（IV）促进反应生成8-烷氧基-7-羟基-四氢咔啉。然而，由BF 3促进的反应产生取代的苯并呋喃。Ti（IV）-或BF 3促进的2-烷氧基-1-（N-苯甲酰基）-4-（N-苯磺酰基）-1,4-苯醌双亚胺的反应也提供了取代的四烃基衍生物。©1997爱思唯尔科学有限公司。