4-methoxy-1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridine | 196882-97-0

• 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: 4-methoxy-1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 1-(benzenesulfonyl)-4-methoxy-3,6-dihydro-2H-pyridine
• CAS: 196882-97-0
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: BSXUBCDLHLNNCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridine 在 titanium(IV) isopropylate 、 selenium(IV) oxide 、 sodium acetate 、 四氯化钛 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 139.0h， 生成 1-(7,8-Dimethoxy-2-oxy-pyrido[4,3-b]indol-5-yl)-ethanone
  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：

  4-氧代哌啶酮盐酸盐 在 三氯化铝 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 氯仿 、 水 为溶剂， 反应 87.0h， 生成 4-methoxy-1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridine
  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。
• 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.