1,5-diphenyl-1H-naphtho[1,2-d][1,2,3]triazole | 1309447-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-diphenyl-1H-naphtho[1,2-d][1,2,3]triazole
• CAS: 1309447-86-6
• 化学式: C₂₂H₁₅N₃
• 分子量: 321.381
• InChiKey: JSUXRLCNGZKUTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1，4-二苯基丁二炔 、 叠氮苯 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以42%的产率得到1,5-diphenyl-1H-naphtho[1,2-d][1,2,3]triazole
  参考文献：
  名称：

  Unprecedented Cu-Catalyzed Coupling of Internal 1,3-Diynes with Azides: One-Pot Tandem Cyclizations Involving 1,3-Dipolar Cycloaddition and Carbocyclization Furnishing Naphthotriazoles

  摘要：

  A one-pot protocol for the synthesis of triazole-annulated polyheterocycles via metal-catalyzed coupling of internal 1,4-disubstituted 1,3-diynes and organic azides has been described. The mechanistic rationale for the reaction suggests tandem cyclizations involving copper-catalyzed cycloaddition and 6-endo carbocyclization reactions. The cascade cyclization leads to an increase in molecular complexity to furnish naphtho[1,2-d]triazoles in satisfactory yields. The generality of the method has been demonstrated by using a series of aromatic/aliphatic azides and symmetrical internal 1,3-diynes.

  DOI：

  10.1021/ol201092k