2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]pyridine | 1310414-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]pyridine
• 英文别名: [(4-CH2Ph-1H-1,2,3-triazol-4-yl)methyl]pyridine；2-[(4-Benzyltriazol-1-yl)methyl]pyridine；2-[(4-benzyltriazol-1-yl)methyl]pyridine
• CAS: 1310414-58-4
• 化学式: C₁₅H₁₄N₄
• 分子量: 250.303
• InChiKey: ORHZQMDFPQRSHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]pyridine 以 甲醇 为溶剂， 反应 16.0h， 以95%的产率得到fac-[Re(CO)₃Cl(2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]pyridine)]
  参考文献：
  名称：

  [2-（4-R-1 H -1,2,3-三唑-1-基）甲基]吡啶的fac- Re（CO）3 Cl络合物逆“点击”配体：系统合成，光谱和计算学习

  摘要：

  通过回流[Re（CO）5 Cl的甲醇溶液，已经合成了一系列电子调谐的fac -Re（CO）3 Cl反吡啶-1,2,3-三唑复合物，收率好至极好（72–95％）。]和取代的[2-（4-R-1 H -1,2,3-三唑-1-基）甲基]吡啶配体（py（CH 2）tri-R）。所得rh（I）配合物通过元素分析，HR-ESI-MS和IR以及1 H和13 C NMR光谱进行表征。另外，使用X射线晶体学证实了三种配合物的分子结构。该系列的fac- [（py（CH 2）tri-R）Re（CO）3的电子性质使用紫外可见光谱，拉曼光谱，发射光谱法和循环伏安法对Cl]络合物进行了检测。配合物在紫外线区域表现出强烈的吸收，这是使用时间依赖的密度泛函理论（TD-DFT）进行建模的。计算结果表明，吸收带的较低能量部分实际上是MLCT，并且存在更高的π–π *跃迁。除R = 4-硝基苯基外，所有电子光谱几乎相同，这表明1

  DOI：

  10.1021/om300868k
• 作为产物：
  描述：

  3-苯-1-丙炔 、 2-(溴甲基)吡啶氢溴酸盐 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium carbonate 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以83%的产率得到2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]pyridine
  参考文献：
  名称：

  Palladium(II) Complexes of Readily Functionalized Bidentate 2-Pyridyl-1,2,3-triazole “Click” Ligands: A Synthetic, Structural, Spectroscopic, and Computational Study

  摘要：

  The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes, the CuAAC "click" reaction is currently receiving considerable attention as a mild, modular method for the generation of functionalized ligand scaffolds. Herein we show that mild one-pot "click" methods can be used to readily and rapidly synthesize a family of functionalized bidentate 2-pyridyl-1,2,3-triazole ligands, containing electrochemically, photochemically, and biologically active functional groups in good to excellent yields (47-94%). The new ligands have been fully characterized by elemental analysis, HR-ESI-MS, IR, H-1 and C-13 NMR and in three cases by X-ray crystallography. Furthermore we have demonstrated that this family of functionalized "click" ligands readily form bis-bidentate Pd(II)/complexes. Solution studies, X-ray crystallography, and density functional theory (DFT) calculations indicate that the Pd(II) complexes formed with the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine series of ligands are more stable than those formed with the [4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine "click" ligands.

  DOI：

  10.1021/ic200789b

文献信息

• Palladium(II) Complexes of Readily Functionalized Bidentate 2-Pyridyl-1,2,3-triazole “Click” Ligands: A Synthetic, Structural, Spectroscopic, and Computational Study
  作者：Kelly J. Kilpin、Emma L. Gavey、C. John McAdam、Christopher B. Anderson、Samuel J. Lind、Courtney C. Keep、Keith C. Gordon、James D. Crowley

  DOI：10.1021/ic200789b

  日期：2011.7.4

  The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes, the CuAAC "click" reaction is currently receiving considerable attention as a mild, modular method for the generation of functionalized ligand scaffolds. Herein we show that mild one-pot "click" methods can be used to readily and rapidly synthesize a family of functionalized bidentate 2-pyridyl-1,2,3-triazole ligands, containing electrochemically, photochemically, and biologically active functional groups in good to excellent yields (47-94%). The new ligands have been fully characterized by elemental analysis, HR-ESI-MS, IR, H-1 and C-13 NMR and in three cases by X-ray crystallography. Furthermore we have demonstrated that this family of functionalized "click" ligands readily form bis-bidentate Pd(II)/complexes. Solution studies, X-ray crystallography, and density functional theory (DFT) calculations indicate that the Pd(II) complexes formed with the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine series of ligands are more stable than those formed with the [4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine "click" ligands.
• <i>fac-</i>Re(CO)₃Cl Complexes of [2-(4-R-1<i>H</i>-1,2,3-Triazol-1-yl)methyl]pyridine Inverse “Click” Ligands: A Systematic Synthetic, Spectroscopic, and Computational Study
  作者：Christopher B. Anderson、Anastasia B. S. Elliott、C. John McAdam、Keith C. Gordon、James D. Crowley

  DOI：10.1021/om300868k

  日期：2013.2.11

  crystallography. The electronic properties of this series of fac-[(py(CH2)tri-R)Re(CO)3Cl] complexes were examined using UV–vis, Raman, and emission spectroscopy and cyclic voltammetry techniques. The complexes exhibit intense absorptions in the UV region, which were modeled using time-dependent density functional theory (TD-DFT). The calculations suggest that the lower energy part of the absorption band is MLCT

  通过回流[Re（CO）5 Cl的甲醇溶液，已经合成了一系列电子调谐的fac -Re（CO）3 Cl反吡啶-1,2,3-三唑复合物，收率好至极好（72–95％）。]和取代的[2-（4-R-1 H -1,2,3-三唑-1-基）甲基]吡啶配体（py（CH 2）tri-R）。所得rh（I）配合物通过元素分析，HR-ESI-MS和IR以及1 H和13 C NMR光谱进行表征。另外，使用X射线晶体学证实了三种配合物的分子结构。该系列的fac- [（py（CH 2）tri-R）Re（CO）3的电子性质使用紫外可见光谱，拉曼光谱，发射光谱法和循环伏安法对Cl]络合物进行了检测。配合物在紫外线区域表现出强烈的吸收，这是使用时间依赖的密度泛函理论（TD-DFT）进行建模的。计算结果表明，吸收带的较低能量部分实际上是MLCT，并且存在更高的π–π *跃迁。除R = 4-硝基苯基外，所有电子光谱几乎相同，这表明1