1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole | 1318914-60-1

• 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: 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole
• 英文别名: 2-(1-Cyclohexyltriazol-4-yl)pyridine
• CAS: 1318914-60-1
• 化学式: C₁₃H₁₆N₄
• 分子量: 228.297
• InChiKey: GDRHENSQXHYPQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole 以 硝基甲烷 为溶剂， 以51%的产率得到dichloro(1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole)platinum(II)
  参考文献：
  名称：

  Expanding the scope of ‘Click’ derived 1,2,3-triazole ligands: New palladium and platinum complexes

  摘要：

  Using the 'Click Protocol' the new ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (3), 1-(2-mercaptomethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (4) and 1-(4-N, N-dimethylamino phenyl)-4-(2-pyridyl)-1,2,3-triazole (5) were prepared by reacting 2-ethynylpyridine with the corresponding azides. In the next step the ligands were reacted with suitable palladium and platinum precursors to yield the cis-dichloro-palladium complexes 1a-4a and platinum complexes 1b-4b. Investigation of the molecular structure of the free ligands 1 and 5 reveals the formation of infinite chains in the 3D structure which are governed by hydrogen bonds between the triazole units. Likewise the 3D structure of 1a shows infinite chains which are held together by multiple remarkably short C-H center dot center dot center dot Cl-Pd contacts. Electrochemical investigation of the free ligands by cyclic voltammetry showed irreversible reduction processes at highly negative potential. Upon metal complexation huge anodic shifts of the reduction potential were observed. To further characterize the electronic properties of all the compounds UV-Vis spectra were also analyzed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.085
• 作为产物：
  描述：

  2-乙炔基吡啶 、 叠氮基环己烷 在 copper(ll) sulfate pentahydrate 、 叔丁基三氯乙酰亚胺酯 、 (+)-sodium L-ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以49%的产率得到1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole
  参考文献：
  名称：

  Expanding the scope of ‘Click’ derived 1,2,3-triazole ligands: New palladium and platinum complexes

  摘要：

  Using the 'Click Protocol' the new ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2-trifluoromethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-hexyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (3), 1-(2-mercaptomethyl phenyl)-4-(2-pyridyl)-1,2,3-triazole (4) and 1-(4-N, N-dimethylamino phenyl)-4-(2-pyridyl)-1,2,3-triazole (5) were prepared by reacting 2-ethynylpyridine with the corresponding azides. In the next step the ligands were reacted with suitable palladium and platinum precursors to yield the cis-dichloro-palladium complexes 1a-4a and platinum complexes 1b-4b. Investigation of the molecular structure of the free ligands 1 and 5 reveals the formation of infinite chains in the 3D structure which are governed by hydrogen bonds between the triazole units. Likewise the 3D structure of 1a shows infinite chains which are held together by multiple remarkably short C-H center dot center dot center dot Cl-Pd contacts. Electrochemical investigation of the free ligands by cyclic voltammetry showed irreversible reduction processes at highly negative potential. Upon metal complexation huge anodic shifts of the reduction potential were observed. To further characterize the electronic properties of all the compounds UV-Vis spectra were also analyzed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.085

文献信息

• Nickel complexes with “click”-derived pyridyl-triazole ligands: weak intermolecular interactions and catalytic ethylene oligomerisation
  作者：David Schweinfurth、Cheng-Yong Su、Shi-Chao Wei、Pierre Braunstein、Biprajit Sarkar

  DOI：10.1039/c2dt31805a

  日期：——

  The ligands 1-(cyclohexyl)-4-(2-pyridyl)-1,2,3-triazole (1), 1-(2,6-diisopropylphenyl)-4-(2-pyridyl)-1,2,3-triazole (2), 1-(4-butoxyphenyl)-4-(2-pyridyl)-1,2,3-triazole (3) and 1-(methyl)-4-(2-pyridyl)-1,2,3-triazole (4) were synthesized by the Cu(I) catalyzed “Click” reaction between 2-pyridylacetylene and the corresponding azides. The ligands were then reacted with NiBr2·3H2O to generate the complexes (1)2NiBr2 (1a), (2)2NiBr2 (2a), (3)2NiBr2 (3a) and (4)2NiBr2 (4a). Structural characterization of 1a confirmed the mononuclear and distorted octahedral environment around the Ni(II) center, with the pyridyl-triazole ligands coordinating in a bis-chelating fashion. Bond length analysis inside the 1,2,3-triazole ring shows a short NN double bond that is flanked by two longer C–N and N–N bonds pointing to the existence of “azo” character in the ring. The highly polar five-membered 1,2,3-triazole ring makes its C–H bond acidic, and these bonds participate in an extended weak intermolecular C–H⋯Br interactions with the Br-groups of neighboring molecules, resulting in a 3-D network. The nickel complexes with these “Click” ligands were tested as pre-catalysts for ethylene oligomerization, and the complexes showed moderate activity in that reaction with good selectivity towards C4 oligomers.

  配体1-(环己基)-4-(2-吡啶基)-1,2,3-三唑（1）、1-(2,6-二异丙基苯基)-4-(2-吡啶基)-1,2,3-三唑（2）、1-(4-正丁氧基苯基)-4-(2-吡啶基)-1,2,3-三唑（3）和1-(甲基)-4-(2-吡啶基)-1,2,3-三唑（4）是通过铜(I)催化的“点击”反应，使用2-吡啶乙炔与相应的叠氮化物合成的。然后，将配体与NiBr2·3H2O反应，生成络合物(1)2NiBr2（1a）、(2)2NiBr2（2a）、(3)2NiBr2（3a）和(4)2NiBr2（4a）。1a的结构表征确认了围绕Ni(II)中心的单核和扭曲八面体环境，吡啶-三唑配体呈双螯合方式配位。在1,2,3-三唑环内的键长分析显示了一个短的NN双键，两侧有两个较长的C–N和N–N键，表明环内存在“偶氮”特性。高极性的五元1,2,3-三唑环使其C–H键呈酸性，这些键参与了与相邻分子Br基团之间的扩展弱分子间C–H···Br相互作用，形成了三维网络。这些“点击”配体的镍络合物作为乙烯聚合的前催化剂进行了测试，结果显示这些络合物在此反应中表现出适度的活性，并对C4寡聚物具有良好的选择性。