ethyl 1-(adamantan-1-yl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate | 1429172-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(adamantan-1-yl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate
• CAS: 1429172-00-8
• 化学式: C₂₁H₂₅N₃O₂
• 分子量: 351.448
• InChiKey: IHBSOSUYEDTSEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.01
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  叠氮金刚烷 、 苯丙炔酸乙酯 在 [Cu₈(μ₄-H){S₂P(OEt)₂}₆](PF₆) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 ethyl 1-(adamantan-1-yl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate 、 ethyl 1-(adamantan-1-yl)-4-phenyl-1H-1,2,3-triazole-5-carboxylate
  参考文献：
  名称：

  [Cu8(μ4-H){S2P(OEt)2}6](PF6): A Novel Catalytic Hydride-Centered Copper Cluster for Azide-Alkyne Cycloaddtion

  摘要：

  A hydride-centered dithiophosphate cluster [Cu-8(mu(4)-H){S2P(OEt)(2)}(6)](PF6) (1)] previously developed by us was applied as a new catalyst to the 1,3-dipolar cycloaddition of organic azides and alkynes for preparing substituted trizoles. With the required catalyst loading as low as 0.4 mol%, the reactions of terminal alkynes with BnN3 all proceeded smoothly at ambient temperature in CH3CN to exclusively produce 1,4-triazoles in good yields. For these reactions, it is assumed that the formation of the requisite copper acetylide intermediate is facilitated by the abstraction of the terminal hydrogen of alkynes by the hydride released from the central of the cluster. With only few examples being documented in literatures, the reactions of a range of internal alkynes have also been realized under the catalysis of 1 (0.8 mol%) in DMF at elevated temperature, to yield 1,4,5-trisubstituted triazoles in moderate to high yields. Our study has provided a preliminary insight into the effect of sulfur-based ligands on the activity of copper ion.

  DOI：

  10.1007/s10562-013-0993-7