1-benzyl-1,2,3,4-tetrahydro-β-carboline | 99545-51-4

• 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: 1-benzyl-1,2,3,4-tetrahydro-β-carboline
• 英文别名: (S)-1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole；(S)-1-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole；(R,S)-1-Benzyl-2,3,4,9-tetrahydro-1H-I(2)-carboline；(1S)-1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 99545-51-4
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: LHVNPTMRAQQPID-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  色胺盐酸盐 、 苯乙醛 在 Ophiorrhiza pumila strictosidine synthase 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 1-benzyl-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Biocatalytic asymmetric formation of tetrahydro-β-carbolines

  摘要：

  Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetlet.2010.06.075

文献信息

• Catalytic Asymmetric Pictet–Spengler Reactions via Sulfenyliminium Ions
  作者：Martin J. Wanner、Richard N. S. van der Haas、Kimberly R. de Cuba、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1002/anie.200701808

  日期：2007.10.1
• Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
  作者：Marlene Espinoza-Moraga、Tania Petta、Marco Vasquez-Vasquez、V. Felipe Laurie、Luis A.B. Moraes、Leonardo Silva Santos

  DOI：10.1016/j.tetasy.2010.06.036

  日期：2010.8

  beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C-1-C-11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C-15 and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.
• Biocatalytic asymmetric formation of tetrahydro-β-carbolines
  作者：Peter Bernhardt、Aimee R. Usera、Sarah E. O’Connor

  DOI：10.1016/j.tetlet.2010.06.075

  日期：2010.8

  Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved