(1S)-1-(1,3-benzodioxol-5-yl)-2-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole | 1040446-56-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S)-1-(1,3-benzodioxol-5-yl)-2-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 1040446-56-7
• 化学式: C₂₅H₂₂N₂O₂
• 分子量: 382.462
• InChiKey: PADQVXMSUCCBAI-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒醛 、 苄基-[2-(1H-吲哚-3-基)-乙基]-胺 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (R)-1-(3,4-methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline 、 (1S)-1-(1,3-benzodioxol-5-yl)-2-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
  参考文献：
  名称：

  Enantioselective BINOL-Phosphoric Acid Catalyzed Pictet−Spengler Reactions of N-Benzyltryptamine

  摘要：

  [GRAPHICS]Optically active tetrahydro-beta-carbolines were synthesized via an (R)-BINOL-phosphoric acid-catalyzed asynunetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-beta-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5 -bistrifluoromethylphenyL-substituted BINOL-phosphoric acid was identified as the best catalyst.

  DOI：

  10.1021/jo8010478

文献信息

• Enantioselective BINOL-Phosphoric Acid Catalyzed Pictet−Spengler Reactions of <i>N</i>-Benzyltryptamine
  作者：Nishant V. Sewgobind、Martin J. Wanner、Steen Ingemann、René de Gelder、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1021/jo8010478

  日期：2008.8.1

  [GRAPHICS]Optically active tetrahydro-beta-carbolines were synthesized via an (R)-BINOL-phosphoric acid-catalyzed asynunetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-beta-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5 -bistrifluoromethylphenyL-substituted BINOL-phosphoric acid was identified as the best catalyst.