1-hexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

• 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-hexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 化学式: C₁₇H₂₄N₂
• 分子量: 256.391
• InChiKey: UBNGZHIXVPLOOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  色胺 、 正庚醇 在 亚硝酸特丁酯 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 三氟乙酸 作用下， 反应 24.0h， 以44%的产率得到1-hexyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  通过基于酒精的直接和温和的好氧氧化 Pictet-Spengler 反应选择性构建生物碱支架。

  摘要：

  采用TBN/TEMPO作为催化剂，氧气作为氧化剂，以前通过多步工艺获得的具有生物学和药学意义的四氢-β-咔啉和β-咔啉生物碱支架现在可以通过一步选择性获得在温和的条件下，色胺与醇的直接需氧氧化 Pictet-Spengler 反应，生成水作为副产物。在该反应中，有趣地发现 TBN/TEMPO 能够促进整个反应的环化步骤。这种方法可以容忍多种C - 和N-取代的色胺，以及反应性更强的苄醇和烯丙醇以及反应性较低的脂肪醇。该方法还可以扩展到二氢-β-咔啉的合成，并应用于更容易获得和更经济的色氨酸合成β-咔啉，揭示了其广泛的底物范围和合成应用潜力。

  DOI：

  10.1039/d0ob01549k

文献信息

• Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives
  作者：Nicole Sudžuković、Johann Schinnerl、Lothar Brecker

  DOI：10.1016/j.bmc.2015.12.028

  日期：2016.2

  Synthesis of 13 different tetrahydro-beta-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and L-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of a-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-beta-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products. (c) 2015 Elsevier Ltd. All rights reserved.
• Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions
  作者：Haicheng Liu、Feng Han、Huan Li、Jianping Liu、Qing Xu

  DOI：10.1039/d0ob01549k

  日期：——

  Employing TBN/TEMPO as the catalysts and oxygen as the oxidant, the biologically and pharmaceutically significant tetrahydro-β-carboline and β-carboline alkaloid scaffolds that used to be obtained by multi-step processes can now be selectively obtained in only one-step via direct aerobic oxidative Pictet–Spengler reactions of tryptamines with alcohols under mild conditions, with water generated as

  采用TBN/TEMPO作为催化剂，氧气作为氧化剂，以前通过多步工艺获得的具有生物学和药学意义的四氢-β-咔啉和β-咔啉生物碱支架现在可以通过一步选择性获得在温和的条件下，色胺与醇的直接需氧氧化 Pictet-Spengler 反应，生成水作为副产物。在该反应中，有趣地发现 TBN/TEMPO 能够促进整个反应的环化步骤。这种方法可以容忍多种C - 和N-取代的色胺，以及反应性更强的苄醇和烯丙醇以及反应性较低的脂肪醇。该方法还可以扩展到二氢-β-咔啉的合成，并应用于更容易获得和更经济的色氨酸合成β-咔啉，揭示了其广泛的底物范围和合成应用潜力。