phenyl 3-(5-phenyl-1H-naphtho[1,2-d][1,2,3]triazol-1-yl)propyl ether | 1309447-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: phenyl 3-(5-phenyl-1H-naphtho[1,2-d][1,2,3]triazol-1-yl)propyl ether
• 英文别名: 1-(3-Phenoxypropyl)-5-phenylbenzo[e]benzotriazole；1-(3-phenoxypropyl)-5-phenylbenzo[e]benzotriazole
• CAS: 1309447-93-5
• 化学式: C₂₅H₂₁N₃O
• 分子量: 379.461
• InChiKey: AVSSAYUIIHJXMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1，4-二苯基丁二炔 、 (3-azidopropoxy)benzene 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以52%的产率得到phenyl 3-(5-phenyl-1H-naphtho[1,2-d][1,2,3]triazol-1-yl)propyl ether
  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

文献信息

• Unprecedented Cu-Catalyzed Coupling of Internal 1,3-Diynes with Azides: One-Pot Tandem Cyclizations Involving 1,3-Dipolar Cycloaddition and Carbocyclization Furnishing Naphthotriazoles
  作者：Anil K. Mandadapu、Sudhir K. Sharma、Sahaj Gupta、Deevi G Venkata Krishna、Bijoy Kundu

  DOI：10.1021/ol201092k

  日期：2011.6.17

  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.