9-methyl-4-(4-chlorophenyl)-2-tosyl-1,2,3,4-tetrahydro-β-carboline | 1434620-89-9

• 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-methyl-4-(4-chlorophenyl)-2-tosyl-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 9-methyl-4-phenyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole；4-(4-chlorophenyl)-9-methyl-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 1434620-89-9
• 化学式: C₂₅H₂₃ClN₂O₂S
• 分子量: 450.989
• InChiKey: UWMKDJHNLJWEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine 在 六氟磷酸银 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 9-methyl-4-(4-chlorophenyl)-2-tosyl-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Lewis acid promoted three-component reactions of aziridines, arenes and aldehydes: an efficient and diastereoselective synthesis of cis-1,4-disubstituted tetrahydroisoquinolines

  摘要：

  A new Lewis acid promoted three-component reaction between the aziridine, arene and aldehyde has been developed. This reaction involves sequential ring opening of aziridine and Pictet-Spengler condensation and gives a broad range of cis-1,4-disubstituted tetrahydroisoquinolines in moderate yields with good diastereoselectivities under mild conditions. The methodology provides a rapid and convergent synthesis for the scaffold of tetrahydroisoquinoline and serves as a good tool for constructing the libraries of substituted tetrahydroisoquinolines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.013

文献信息

• A Novel Lewis Acid Catalyzed [3 + 3]-Annulation Strategy for the Syntheses of Tetrahydro-β-Carbolines and Tetrahydroisoquinolines
  作者：Shaoyin Wang、Zhuo Chai、Shuangliu Zhou、Shaowu Wang、Xiancui Zhu、Yun Wei

  DOI：10.1021/ol4008525

  日期：2013.6.7

  process for the efficient syntheses of both tetrahydro-β-carbolines and tetrahydroisoquinolines from readily available benzylic alcohols and aziridines was developed, which would be a highly valuable complement to the widely used Pictet–Spengler reaction. A probable mechanism was proposed based on the isolation and characterization of two key intermediates. This strategy enables facile access to important

  一种新颖的路易斯酸催化的[3 + 3]环化工艺，用于由易得的苯甲醇和氮丙啶有效合成四氢-β-咔啉和四氢异喹啉，这将是广泛使用的Pictet-Spengler的极有价值的补充反应。基于两种关键中间体的分离和表征，提出了一种可能的机制。这种策略使得可以轻松访问其他已知方法无法轻易获得的重要生物碱框架。