4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)-1H-pyrazole-5-carboxylate | 1450980-81-0

• 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: 4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)-1H-pyrazole-5-carboxylate
• 英文别名: 4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)-1H-pyrazole-5-carboxylic acid
• CAS: 1450980-81-0
• 化学式: C₁₅H₁₄N₄O₂
• 分子量: 282.302
• InChiKey: XIAOLBJYGAJDDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  色胺 、 4-甲酰-1H-吡唑-5-羧酸 在 硼酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Comparative evaluation of a Pictet–Spengler protocol in microwave-assisted conversions of tryptamine with aryl- and carboxyaryl aldehydes: role of ring strain in cyclocondensation of the primarily formed carboxyaryl-substituted β-carbolines

  摘要：

  An efficient microwave-assisted Pictet-Spengler protocol employing boric acid/acetic acid as a catalytic system was elaborated for the synthesis of 1-aryl-beta-carbolines. Under the novel conditions tryptamine and 2-formylbenzoic acid furnished a pentacyclic skeleton in a single step, whereas using o-phthalaldehyde as a coupling partner led to the formation of an isoindolone derivative. Three beta-carbolines primarily resulted from the reactions involving carboxy-substituted heteroaryl aldehydes and avoided cyclisation to polycondensed skeletons with enhanced ring strain, as was evidenced by density functional theory (DFT) modelling.

  DOI：

  10.1007/s00706-013-1007-6