N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazolium chloride | 1419605-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazolium chloride
• 英文别名: N-[2-(pyrazol-1-yl)phenyl]-N-benzylimidazolium chloride；1-benzyl-3-(2-pyrazol-1-ylphenyl)imidazol-1-ium;chloride
• CAS: 1419605-67-6
• 化学式: C₁₉H₁₇N₄*Cl
• 分子量: 336.824
• InChiKey: YFSOADOLINICOM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.0
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazolium chloride 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以60%的产率得到N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazol-2-ylidene palladium chloride
  参考文献：
  名称：

  Synthesis and catalytic activity of pyrazolyl-functionalized N-heterocyclic carbene palladium complexes

  摘要：

  基于1-[2-(吡唑-1-基)苯基]咪唑的三种吡唑功能化的N-杂环卡宾(NHC)钯配合物已通过物理化学和光谱方法合成并表征，其中两种配合物的结构经单晶X射线衍射确认。吡唑功能化的NHC在这些配合物中充当螯合的N,C-双齿配体。催化测试证明，这些配合物在空气下水中或水/有机溶剂中对铃木-宫浦和沟吕木- Heck偶联反应表现出极高的催化活性。吡唑环上的取代基对这些偶联反应中配合物的催化活性产生不同影响。

  DOI：

  10.1007/s11243-013-9784-7
• 作为产物：
  描述：

  1-(2-iodophenyl)-1H-pyrazole 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 72.0h， 生成 N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazolium chloride
  参考文献：
  名称：

  Synthesis and catalytic activity of N-heterocyclic carbene silver complexes derived from 1-[2-(pyrazol-1-yl)phenyl]imidazole

  摘要：

  Six mono-and dinuclear N-heterocyclic carbene (NHC) silver complexes based on 1-[2-(pyrazol-1-yl) phenyl] imidazole have been synthesized and characterized by elemental analysis and NMR spectroscopy, and their structures have been confirmed by single crystal X-ray diffraction. The N-functionalized carbene ligands exhibit versatile coordination modes in these silver complexes. N-[2-(3,5-Dimethylpyrazol-1-yl)phenyl]-N-benzylimidazol-2-ylidene (L) acts as a monodentate ligand through the carbene carbon in mononuclear LAgCl. While in dinuclear L2Ag2(PF6)(2) and L'Ag-2(2)(PF6)(2) (L' = N-[2-(pyrazol-1-yl) phenyl]-N-benzylimidazol-2-ylidene), L and L' act as bridging bidentate ligands through the pyrazolyl nitrogen and the carbene carbon atoms to two silver atoms. Though, these two silver atoms have different coordination environments. In the former, one silver atom coordinates with two carbene carbons, the other coordinates with two pyrazolyl nitrogen atoms. In the latter, each silver atom coordinates with one carbene carbon and one pyrazolyl nitrogen atom, respectively. A dinuclear macrocyclic structure is observed in m-xylyl bridging tetradentate bis-NHC complexes L2Ag2(BF4)(2) and (L)CH2C6H4CH2(L)Ag-2(BF4)(2), in which the coordination mode of carbene ligands is similar with that in L2Ag2(PF6)(2). Preliminary catalytic tests show that all these complexes exhibit highly effective catalytic activity in the three-component coupling reaction of alkyne, aldehyde and amine forming propargylamines. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.12.008