2-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-phenol

• 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: 2-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-phenol
• 英文别名: 2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenol；2-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-phenol；1-<2-Hydroxy-phenyl>-1,2,3,4-tetrahydro-β-carbolin；2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenolate
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: DLRFYHZDPBAQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-phenol 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 反应 12.0h， 以76%的产率得到2-(9H-pyrido[3,4-b]indol-1-yl)phenol
  参考文献：
  名称：

  空气下四氢-β-咔啉有机碱促进的高效脱氢/脱羧芳构化

  摘要：

  已确认有机碱DBN是在空气气氛下促进四氢-β-咔啉的脱氢/脱羧芳构化的有效试剂，以中等到良好的产率获得相应的β-咔啉。还证明了该方案可用于以克级合成β-咔啉生物碱eudistomin U（7）和harmane（10）。

  DOI：

  10.1016/j.tetlet.2019.02.020
• 作为产物：
  描述：

  色胺 、 水杨醛 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到2-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-phenol
  参考文献：
  名称：

  空气下四氢-β-咔啉有机碱促进的高效脱氢/脱羧芳构化

  摘要：

  已确认有机碱DBN是在空气气氛下促进四氢-β-咔啉的脱氢/脱羧芳构化的有效试剂，以中等到良好的产率获得相应的β-咔啉。还证明了该方案可用于以克级合成β-咔啉生物碱eudistomin U（7）和harmane（10）。

  DOI：

  10.1016/j.tetlet.2019.02.020

文献信息

• Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction
  作者：Ashish Sharma、Mrityunjay Singh、Nitya Nand Rai、Devesh Sawant

  DOI：10.3762/bjoc.9.140

  日期：——

  Pictet-Spengler reaction catalyzed by cyanuric chloride (trichloro-1,3,5-triazine, TCT) is described. The 6-endo cyclization of tryptophan/tryptamine and modified Pictet-Spengler substrates with both electron-withdrawing and electron-donating aldehydes was carried out by using a catalytic amount of TCT (10 mol %) in DMSO under a nitrogen atmosphere. TCT catalyzed the Pictet-Spengler reaction involving electron-donating

  描述了一种由氰尿酰氯 (三氯-1,3,5-三嗪, TCT) 催化的 Pictet-Spengler 反应的实用、温和和有效的协议。色氨酸/色胺和修饰的 Pictet-Spengler 底物与吸电子醛和给电子醛的 6-内环化是通过在氮气氛下在 DMSO 中使用催化量的 TCT（10 mol%）进行的。TCT 以优异的产率催化了涉及给电子醛的 Pictet-Spengler 反应。因此，与现有的供电子醛不能进行 6-内环化的方法相比，它具有明显的优势。我们的方法提供了广泛的底物范围和多样性。这确实是首次报道使用 TCT 作为 Pictet-Spengler 反应的催化剂。
• Water as an efficient medium for the synthesis of tetrahydro-β-carbolines via Pictet–Spengler reactions
  作者：Biswajit Saha、Sunil Sharma、Devesh Sawant、Bijoy Kundu

  DOI：10.1016/j.tetlet.2006.12.112

  日期：2007.2

  A mild and efficient protocol for the Pictet-Spengler reaction in water using an acid catalyst has been described. The condensation of tryptophan, tryptamine, and N-b-benzyl tryptophan with different aldehydes having both electron-withdrawing and -donating substituents in the presence of a catalytic amount of TFA in water furnished tetrahydro-beta-carbolines in good isolated yields. A salient feature of the water mediated Pictet-Spengler reaction was the general trend observed during the condensation of Trp-OMe and aryl/aliphatic aldehydes furnishing diastereomeric mixtures with a preference for the cis-isomer. (c) 2007 Elsevier Ltd. All rights reserved.
• 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..
• Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines into β-carbolines under air
  作者：Ziquan Zhao、Yan Sun、Lilin Wang、Xuan Chen、Yanpei Sun、Long Lin、Yulin Tang、Fei Li、Dongyin Chen

  DOI：10.1016/j.tetlet.2019.02.020

  日期：2019.3

  DBN has been identified as an efficient reagent for promoting the dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines under air atmosphere, to access the corresponding β-carbolines in moderate to good yields. The utility of this protocol for the gram-scale synthesis of β-carboline alkaloids eudistomin U (7) and harmane (10) has also been demonstrated.

  已确认有机碱DBN是在空气气氛下促进四氢-β-咔啉的脱氢/脱羧芳构化的有效试剂，以中等到良好的产率获得相应的β-咔啉。还证明了该方案可用于以克级合成β-咔啉生物碱eudistomin U（7）和harmane（10）。