1-benzyl-4-(phenanthren-1-yl)-1H-1,2,3-triazole | 1384109-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-benzyl-4-(phenanthren-1-yl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-phenanthren-1-yltriazole；1-benzyl-4-phenanthren-1-yltriazole
• CAS: 1384109-03-8
• 化学式: C₂₃H₁₇N₃
• 分子量: 335.408
• InChiKey: UQBBWFYYZDLERQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-ethynylphenanthrene 、 苄基叠氮 在 RuH(η2-BH4)(CO)(PCy3)2 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以93%的产率得到1-benzyl-4-(phenanthren-1-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Selective Formation of 1,4-Disubstituted Triazoles from Ruthenium-Catalyzed Cycloaddition of Terminal Alkynes and Organic Azides: Scope and Reaction Mechanism

  摘要：

  The catalytic activity of a series of ruthenium complexes lacking cyclopentadienyl ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,4-disubstituted 1,2,3-triazoles. The complex RuH(eta(2)-BH4)(CO)(PCy3)(2) was found to be an effective catalyst for the cycloaddition reactions. In the presence of RuH(eta(2)-BH4)(CO)(PCy3)(2), primary and secondary azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,4-disubstituted 1,2,3-triazoles. The ruthenium-catalyzed azide-alkyne cycloaddition appears to proceed via a Ru-acetylide species as the key intermediate, which undergoes formal cycloaddition with an azide to give a ruthenium triazolide complex. The 1,4-disubstituted 1,2,3-triazole product is generated by metathesis of the triazolide complex with a terminal alkyne. In support of the reaction mechanism, the acetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3) reacts cleanly with benzyl azide to give a ruthenium triazolide complex, which reacts with excess tert-butylacetylene in the presence of PPh3 to give 4-tert-butyl-1-benzyl-1,2,3-triazole and the diacetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3). The mechanism is also supported by DFT calculations.

  DOI：

  10.1021/om300513w

文献信息

• Selective Formation of 1,4-Disubstituted Triazoles from Ruthenium-Catalyzed Cycloaddition of Terminal Alkynes and Organic Azides: Scope and Reaction Mechanism
  作者：Pei Nian Liu、Juan Li、Fu Hai Su、Kun Dong Ju、Li Zhang、Chuan Shi、Herman H. Y. Sung、Ian D. Williams、Valery V. Fokin、Zhenyang Lin、Guochen Jia

  DOI：10.1021/om300513w

  日期：2012.7.9

  The catalytic activity of a series of ruthenium complexes lacking cyclopentadienyl ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,4-disubstituted 1,2,3-triazoles. The complex RuH(eta(2)-BH4)(CO)(PCy3)(2) was found to be an effective catalyst for the cycloaddition reactions. In the presence of RuH(eta(2)-BH4)(CO)(PCy3)(2), primary and secondary azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,4-disubstituted 1,2,3-triazoles. The ruthenium-catalyzed azide-alkyne cycloaddition appears to proceed via a Ru-acetylide species as the key intermediate, which undergoes formal cycloaddition with an azide to give a ruthenium triazolide complex. The 1,4-disubstituted 1,2,3-triazole product is generated by metathesis of the triazolide complex with a terminal alkyne. In support of the reaction mechanism, the acetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3) reacts cleanly with benzyl azide to give a ruthenium triazolide complex, which reacts with excess tert-butylacetylene in the presence of PPh3 to give 4-tert-butyl-1-benzyl-1,2,3-triazole and the diacetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3). The mechanism is also supported by DFT calculations.