1-undecyl-4,9-dihydro-3H-beta-carboline | 924778-54-1

• 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-undecyl-4,9-dihydro-3H-beta-carboline
• 英文别名: 1-undecyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• CAS: 924778-54-1
• 化学式: C₂₂H₃₂N₂
• 分子量: 324.509
• InChiKey: HMNFXHKSTGFRPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-undecyl-4,9-dihydro-3H-beta-carboline 在 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 以63%的产率得到(R)-1-undecyl-1,2,3,4,-tetrahydro-9H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)

  摘要：

  Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe beta-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.003
• 作为产物：
  描述：

  色胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-undecyl-4,9-dihydro-3H-beta-carboline
  参考文献：
  名称：

  Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)

  摘要：

  Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe beta-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.003

文献信息

• 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.
• Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)
  作者：Yaneris Mirabal-Gallardo、Maria del Pilar C. Soriano、Leonardo S. Santos

  DOI：10.1016/j.tetasy.2013.03.003

  日期：2013.4

  Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe beta-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed. (C) 2013 Elsevier Ltd. All rights reserved.