5-methyl-1-phenyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazole-4-carboxamide | 1586765-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-1-phenyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazole-4-carboxamide
• 英文别名: 5-methyl-1-phenyl-N-[2-(5-fluoro-1h-indol-3-yl) ethyl]-1h-1,2,3-triazole-4-carboxamide；N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-5-methyl-1-phenyltriazole-4-carboxamide
• CAS: 1586765-11-8
• 化学式: C₂₀H₁₈FN₅O
• 分子量: 363.394
• InChiKey: QNKDHAVTSOXMME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-1-phenyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazole-4-carboxamide 在 四磷十氧化物 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以74%的产率得到1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-6-fluoro-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives

  摘要：

  Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-beta-carbolines that can be transformed into beta-carboline and tetrahydro-beta-carboline derivatives.

  DOI：

  10.1134/s1070428014020225
• 作为产物：
  描述：

  5-甲基-1-苯基-1H-[1,2,3]三唑-4-甲酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 5-methyl-1-phenyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives

  摘要：

  Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-beta-carbolines that can be transformed into beta-carboline and tetrahydro-beta-carboline derivatives.

  DOI：

  10.1134/s1070428014020225

文献信息

• Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives
  作者：N. T. Pohodylo、V. S. Matiichuk、M. D. Obushak

  DOI：10.1134/s1070428014020225

  日期：2014.2

  Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-beta-carbolines that can be transformed into beta-carboline and tetrahydro-beta-carboline derivatives.