cis-1-(2-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 234117-12-5

• 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: cis-1-(2-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: cis-1-(2-hydroxyphenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline；1-(2-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester；cis-3-(Methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-(2-hydroxybenzol)；methyl (1S,3S)-1-(2-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 234117-12-5
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: XAVCGIXOYOYBPX-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三光气 、 cis-1-(2-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 以 二氯甲烷 为溶剂， 以78%的产率得到methyl (1S,12S)-14-oxo-15-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16,18,20-heptaene-12-carboxylate
  参考文献：
  名称：

  Synthesis of polycyclic indolic structures

  摘要：

  We report the development of routes for the synthesis of three types of polycyclic indolic compounds, all possessing a tetrahydro-beta-carboline sub-structure to which an additional 5 or 6-membered heterocycle is attached across the 1,2-positions of ring C; ail three routes involve a Pictet-Spengler reaction as a key step, which can be used to control the stereochemistry of up to 5 chiral centres. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00735-2
• 作为产物：
  描述：

  邻甲基苄醇 在 molecular sieve 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.5h， 生成 cis-1-(2-hydroxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of polycyclic indolic structures

  摘要：

  We report the development of routes for the synthesis of three types of polycyclic indolic compounds, all possessing a tetrahydro-beta-carboline sub-structure to which an additional 5 or 6-membered heterocycle is attached across the 1,2-positions of ring C; ail three routes involve a Pictet-Spengler reaction as a key step, which can be used to control the stereochemistry of up to 5 chiral centres. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00735-2

文献信息

• Simple and efficient synthesis of tetrahydro-β-carbolines via the Pictet–Spengler reaction in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)
  作者：Li-Na Wang、Su-Li Shen、Jin Qu

  DOI：10.1039/c4ra03628j

  日期：——

  1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) can act as both the solvent and the catalyst to effectively promote the Pictet–Spengler reaction.

  1,1,1,3,3,3-六氟-2-丙醇（HFIP）可以作为溶剂和催化剂，有效地促进Pictet-Spengler反应。
• 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.