7-Methoxy-2,5-dihydro-pyrido[4,3-b]indol-1-one | 267666-64-8

• 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-Methoxy-2,5-dihydro-pyrido[4,3-b]indol-1-one
• 英文别名: 7-Methoxy-2,5-dihydropyrido[4,3-b]indol-1-one
• CAS: 267666-64-8
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: GJSFEFHCSMOJSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Methoxy-2,5-dihydro-pyrido[4,3-b]indol-1-one 在 三氯氧磷 作用下， 反应 40.5h， 以61%的产率得到1-chloro-7-methoxy-5H-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
• 作为产物：
  描述：

  2,5-bis-benzenesulfonyl-7-methoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 selenium(IV) oxide 、 sodium acetate 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 7-Methoxy-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

文献信息

• ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE-1 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：[en]LEGOCHEM BIOSCIENCES, INC.

  公开号：WO2023242631A1

  公开（公告）日：2023-12-21

  The present disclosure relates compounds for inhibiting ectonucleotide pyrophosphatase/phosphodiesterase-1 (ENPP-1), or a pharmaceutically acceptable salts thereof.
• 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.