6-(4-tert-butylphenyl)-2,2'-bipyridine | 1160657-79-3

• 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: 6-(4-tert-butylphenyl)-2,2'-bipyridine
• 英文别名: 6-(p-tert-butylphenyl)-2,2'-bipyridyl；2-(4-Tert-butylphenyl)-6-pyridin-2-ylpyridine；2-(4-tert-butylphenyl)-6-pyridin-2-ylpyridine
• CAS: 1160657-79-3
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: BDSDBKCFWBIDBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [Ir(DMSO)₃Cl] 、 6-(4-tert-butylphenyl)-2,2'-bipyridine 以 not given 为溶剂， 生成
  参考文献：
  名称：

  Cyclometalation of 6-Phenyl-2,2′-Bipyridine and Iridium: Synthesis, Characterization, and Reactivity Studies

  摘要：

  Heating the potential tridentate 6-(4-R-phenyl)-2,2'-bipyridine ligand la (R = H), and derivatives 1b (R = CMe3) and 1c (R = OH), with IrCl3 hydrate in 2-methoxyethanol or acetone/H2O gave the unexpected bidentate cyclometalated NC dinuclear complexes [Ir(NC)Cl-2(C5H5N)](2) (2a-cPy), as the major product. Altering the ligand/metal ratio from 1:1 to 2:1 produced a mixture of bis-cyclometalated complexes, Ir(NNC)(NC)Cl (3a,b), with tridentate and bidentate binding modes. Using discrete Ir-I synthons, such as Ir(dmso)(3)Cl or [Ir(cyclooctene)(2)Cl](2), gave a complicated mixture of products. However, when [Ir(C2H4)(2)Cl](2) was used, then the desired tridentate cyclometalated Ir(NNC) complex Ir(NNC)Et(CH4)Cl (4) was synthesized cleanly. The dinuclear complex 2a-Py was converted to the corresponding mononuclear dichloride complexes Ir(NC)(NN)Cl-2 (5a) upon refluxing with 4,4'-di-tert-butylbipyridine in N,N-dimethylacetamide (DMA). Treatment of 5a with ZnMe2 gives Ir(NC)(NNtBu)MeCl (6a). Abstraction of the chloride with AgOTF yields Ir(NC)(NNtBu)MeOTf (7a). Complex 7a undergoes stoichiometric CH activation with arenes and shows catalytic activity for the H/D exchange between benzene and ( trifluoro)acetic acids.

  DOI：

  10.1021/om900014h
• 作为产物：
  描述：

  6-溴-2,2'-联吡啶 、 4-叔丁基苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 三苯基膦 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.0h， 以79%的产率得到6-(4-tert-butylphenyl)-2,2'-bipyridine
  参考文献：
  名称：

  η2-卟啉 Ru(II) π 配合物

  摘要：

  已经合成了高度稳定的 eta(2)-卟啉 Ru(II) pi 复合物。通过卟啉和 Ru 上的平面配体之间的 pi-pi 堆叠相互作用促进了 eta(2) pi 键的形成。钌与卟啉的π配位导致芳香性和电子特性的巨大变化。这些特性可以通过微调钌上的配体来控制。

  DOI：

  10.1021/ja104842h

文献信息

• Cyclometalation of 6-Phenyl-2,2′-Bipyridine and Iridium: Synthesis, Characterization, and Reactivity Studies
  作者：Kenneth J. H. Young、Muhammed Yousufuddin、Daniel H. Ess、Roy A. Periana

  DOI：10.1021/om900014h

  日期：2009.6.22

  Heating the potential tridentate 6-(4-R-phenyl)-2,2'-bipyridine ligand la (R = H), and derivatives 1b (R = CMe3) and 1c (R = OH), with IrCl3 hydrate in 2-methoxyethanol or acetone/H2O gave the unexpected bidentate cyclometalated NC dinuclear complexes [Ir(NC)Cl-2(C5H5N)](2) (2a-cPy), as the major product. Altering the ligand/metal ratio from 1:1 to 2:1 produced a mixture of bis-cyclometalated complexes, Ir(NNC)(NC)Cl (3a,b), with tridentate and bidentate binding modes. Using discrete Ir-I synthons, such as Ir(dmso)(3)Cl or [Ir(cyclooctene)(2)Cl](2), gave a complicated mixture of products. However, when [Ir(C2H4)(2)Cl](2) was used, then the desired tridentate cyclometalated Ir(NNC) complex Ir(NNC)Et(CH4)Cl (4) was synthesized cleanly. The dinuclear complex 2a-Py was converted to the corresponding mononuclear dichloride complexes Ir(NC)(NN)Cl-2 (5a) upon refluxing with 4,4'-di-tert-butylbipyridine in N,N-dimethylacetamide (DMA). Treatment of 5a with ZnMe2 gives Ir(NC)(NNtBu)MeCl (6a). Abstraction of the chloride with AgOTF yields Ir(NC)(NNtBu)MeOTf (7a). Complex 7a undergoes stoichiometric CH activation with arenes and shows catalytic activity for the H/D exchange between benzene and ( trifluoro)acetic acids.
• η²-Porphyrin Ru(II) π Complexes
  作者：Shigeru Yamaguchi、Hiroshi Shinokubo、Atsuhiro Osuka

  DOI：10.1021/ja104842h

  日期：2010.7.28

  been synthesized. The formation of the eta(2) pi bond has been facilitated through pi-pi stacking interactions between the porphyrin and the planar ligand on Ru. pi coordination of ruthenium to porphyrin results in dramatic changes in the aromaticity and electronic properties. These properties are controllable via fine-tuning of the ligand on ruthenium.

  已经合成了高度稳定的 eta(2)-卟啉 Ru(II) pi 复合物。通过卟啉和 Ru 上的平面配体之间的 pi-pi 堆叠相互作用促进了 eta(2) pi 键的形成。钌与卟啉的π配位导致芳香性和电子特性的巨大变化。这些特性可以通过微调钌上的配体来控制。