lauroyl tryptamine | 21469-18-1

• 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: lauroyl tryptamine
• 英文别名: 3-(2-Dodecanoylamino-ethyl)-indol；N-[2-(1H-Indol-3-yl)ethyl]dodecanamide
• CAS: 21469-18-1
• 化学式: C₂₂H₃₄N₂O
• 分子量: 342.525
• InChiKey: MKNMHNBIWPBTTO-UHFFFAOYSA-N

物化性质

• 沸点：
  557.7±33.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lauroyl tryptamine 生成 1-undecyl-4,9-dihydro-3H-beta-carboline
  参考文献：
  名称：

  Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.06.036
• 作为产物：
  描述：

  月桂酸 、 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 lauroyl tryptamine
  参考文献：
  名称：

  Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.06.036

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.
• HUMAN GUT MICROBIOME-DERIVED BIOSYNTHETIC ENZYMES FOR PRODUCTION OF FATTY ACID AMIDES
  申请人：Massachusetts Institute of Technology

  公开号：US20200299738A1

  公开（公告）日：2020-09-24

  Disclosed herein, in some embodiments, are vectors encoding biosynthetic enzymes from gut microbiome-derived bacterium (e.g., Clostridia enzymes), engineered cells comprising the vectors, and methods of using biosynthetic enzymes from gut microbiome-derived bacterium (e.g., Clostridia enzymes) to produce fatty acid amides.
• [EN] HUMAN GUT MICROBIOME-DERIVED BIOSYNTHETIC ENZYMES FOR PRODUCTION OF FATTY ACID AMIDES<br/>[FR] ENZYMES BIOSYNTHÉTIQUES DÉRIVÉES DU MICROBIOME INTESTINAL HUMAIN POUR LA PRODUCTION D'AMIDES D'ACIDES GRAS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2020185627A1

  公开（公告）日：2020-09-17

  Disclosed herein, in some embodiments, are vectors encoding biosynthetic enzymes from gut microbiome-derived bacterium (e.g., Clostridia enzymes), engineered cells comprising the vectors, and methods of using biosynthetic enzymes from gut microbiome- derived bacterium (e.g., Clostridia enzymes) to produce fatty acid amides.
• 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.