DL-盐酸胡秃子碱 | 6678-82-6

• 物质功能分类: 生物化工 - 中草药成分
• 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
• 中文名称: DL-盐酸胡秃子碱
• 英文名称: 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride
• 英文别名: (+/-)-Calligonine hydrochloride；1-methyl-2,3,4,9-tetrahydro-1H-β-carboline; hydrochloride；1-Methyl-2,3,4,9-tetrahydro-1H-β-carbolin; Hydrochlorid；1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole hydrochloride；1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;hydrochloride
• CAS: 6678-82-6
• 化学式: C₁₂H₁₄N₂*ClH
• mdl: MFCD00238593
• 分子量: 222.718
• InChiKey: CWQORCGWGWEVEL-UHFFFAOYSA-N

物化性质

• 熔点：
  267℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  27.8
• 氢给体数：
  3
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  DL-盐酸胡秃子碱 在 5 mol% Pd/C 、 lithium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.1h， 以92%的产率得到哈尔满碱
  参考文献：
  名称：

  四氢-β-咔啉和β-咔啉的微波辅助合成

  摘要：

  开发了一种利用 1,2-二氯乙烷 (DCE) 和三氟乙酸 (TFA) 的微波介导的 Pictet-Spengler 程序，以提供高产率的四氢-β-咔啉盐。反应在 20 分钟或更短的时间内完成，产物以高产率和纯度从溶液中沉淀，无需液-液萃取或柱色谱。这种方法具有广泛的功能，并且可以在毫克到克的范围内进行。随后还利用催化 Pd/C 开发了合成的四氢-β-咔啉到 β-咔啉的后续微波介导的芳构化。芳香化在 60 分钟或更短的时间内完成，大多数底​​物需要最少的纯化。

  DOI：

  10.1002/ejoc.201301580
• 作为产物：
  描述：

  色胺盐酸盐 、 乙醛 生成 DL-盐酸胡秃子碱
  参考文献：
  名称：

  Monoamine Oxidase (MAO-N) Catalyzed Deracemization of Tetrahydro-β-carbolines: Substrate Dependent Switch in Enantioselectivity

  摘要：

  The tetrahydro-beta-carboline (THBC) ring system is an important structural motif found in a large number of bioactive alkaloid natural products. Herein we report a broadly applicable method for the synthesis of enantiomerically pure beta-carbolines via a deracemization procedure employing the D9 and D11 variants of monoamine oxidase from Aspergillus niger (MAO-N) in combination with a nonselective chemical reducing agent. Biotransformations were performed on a preparative scale, leading to the synthesis of optically enriched products in excellent enantiomeric excess (e.e.; up to 99%) and isolated yield (up to 93%). Interestingly, a switch in enantioselectivity associated with the MAO-N variants is observed as the nature of the C-1 substituent of the THBC is varied. Molecular modeling provided an explanation for this observation and highlighted key active site residues which were modified, resulting in an increase in (R)-selectivity associated with the enzyme. These results provide insight into the factors which influence the selectivity of the MAO-N variants, and may offer a platform for future directed evolution projects aimed toward the challenge of engineering (R)-selective amine oxidase biocatalysts.

  DOI：

  10.1021/cs400724g

文献信息

• Application of chlorotrimethylsilane in Pictet–Spengler reaction
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Andrey S. Plaskon、Andrey A. Tolmachev、Radomyr V. Smaliy

  DOI：10.1007/s00706-012-0804-7

  日期：2012.11

  Chlorotrimethylsilane has been found to be an efficient condensing agent in the Pictet-Spengler reaction, affording an extremely straightforward synthetic route to tetrahydro-beta-carboline derivatives and their analogs. The applicability of the method has been studied, and a representative library of structurally diverse products has been created..