4-amino-2,6-bis(quinolin-8-yl)pyridine | 1000860-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-amino-2,6-bis(quinolin-8-yl)pyridine
• 英文别名: 4-amino-2,6-di(quinolin-8-yl)pyridine；4-amino-2,6-(quinolin-8-yl)pyridine；2,6-di(quinolin-8-yl)pyridin-4-amine
• CAS: 1000860-88-7
• 化学式: C₂₃H₁₆N₄
• 分子量: 348.407
• InChiKey: GITBCOKBGLBSQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-2,6-bis(quinolin-8-yl)pyridine 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 以82%的产率得到4-溴-2,6-双(喹啉-8-基)吡啶
  参考文献：
  名称：

  Synthesis and Characterization of 2,6-Di(quinolin-8-yl)pyridines. New Ligands for Bistridentate Ru^II Complexes with Microsecond Luminescent Lifetimes

  摘要：

  The synthesis of 4-substituted and 4-aryl-substituted 2,6-di(quinolin-8-yl)pyridines is described. The tridentate ligands were prepared via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction or via a one-step ring-forming reaction generating the central pyridine ring. X-ray crystal structures and H-1 NMR shifts are discussed and compared to the corresponding data for a Ru-II bistridentate complex. Intramolecular stacking of two quinoline units in the Run complex is suggested by H-1 NMR data and also observed in the X-ray structure.

  DOI：

  10.1021/jo7015373
• 作为产物：
  描述：

  4-硝基-2,6-(喹啉-8-基)吡啶 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 以90%的产率得到4-amino-2,6-bis(quinolin-8-yl)pyridine
  参考文献：
  名称：

  Synthesis and Characterization of 2,6-Di(quinolin-8-yl)pyridines. New Ligands for Bistridentate Ru^II Complexes with Microsecond Luminescent Lifetimes

  摘要：

  The synthesis of 4-substituted and 4-aryl-substituted 2,6-di(quinolin-8-yl)pyridines is described. The tridentate ligands were prepared via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction or via a one-step ring-forming reaction generating the central pyridine ring. X-ray crystal structures and H-1 NMR shifts are discussed and compared to the corresponding data for a Ru-II bistridentate complex. Intramolecular stacking of two quinoline units in the Run complex is suggested by H-1 NMR data and also observed in the X-ray structure.

  DOI：

  10.1021/jo7015373

文献信息

• Facile Synthesis of Bistridentate Ru^II Complexes Based on 2,6-Di(quinolin-8-yl)pyridyl Ligands: Sensitizers with Microsecond ³MLCT Excited State Lifetimes
  作者：Michael Jäger、Rohan J. Kumar、Helmar Görls、Jonas Bergquist、Olof Johansson

  DOI：10.1021/ic802342t

  日期：2009.4.6

  [Ru(dqp)2Cl]+ (28−46%). [Ru(dqp2)Cl]+ was photochemically, or thermally in the presence of AgI, converted to mer-1. By using mer-[Ru(dqp)(MeCN)3] 2+, which was crystallographically characterized, a wide range of homo- and heteroleptic meridional [Ru(dqp)2]2+-based complexes was synthesized in up to 77% yield. The synthetic utility of meridional [Ru(dqp)2]2+-based complexes as building blocks was demonstrated

  研究了基于2,6-二（喹啉-8-基）吡啶基（dqp）配体的子午线双链钌（II）配合物的合成途径。微波辅助合成在200°C时可以高产率（49-87％）制备含有惰性官能团的均化经络[Ru（dqp）2 ] 2+基络合物。应用该协议用于合成聚体-的[Ru（DQP）2 ] 2+（聚体- 1），但将温度降低至180℃并且反应时间短揭示面部异构体的形成顺式，FAC - 1和反式，事实-1（收率分别为56％和12％）。通过NMR光谱和X射线衍射分析表征面部异构体。在逐步操作方案中，Ru（dqp）Cl 3或Ru（dqp）（L）Cl 2（L = MeCN或DMSO）与第二当量dqp的反应以12-26％的收率得到mer - 1和N 5 Cl -配位[Ru（dqp）2 Cl] +（28-46％）。[Ru（dqp 2）Cl] +在Ag I存在下进行了光化学或热反应，转化为mer - 1。通过使用聚体-的[Ru（DQP）（MeCN中）3
• Bistridentate Ruthenium(II)polypyridyl-Type Complexes with Microsecond ³MLCT State Lifetimes: Sensitizers for Rod-Like Molecular Arrays
  作者：Maria Abrahamsson、Michael Jäger、Rohan J. Kumar、Tomas Österman、Petter Persson、Hans-Christian Becker、Olof Johansson、Leif Hammarström

  DOI：10.1021/ja804890k

  日期：2008.11.19

  A series of bistridentate ruthenium(II) polypyridyl-type complexes based on the novel 2,6-di(quinolin-8-yl)pyridine (dqp) ligand have been synthesized and their photophysical properties have been studied. The complexes are amenable to substitution in the 4-position of the central pyridine with conserved quasi-C2v symmetry, which allows for extension to isomer-free, rod-like molecular arrays for vectorial

  合成了一系列基于新型 2,6-二(喹啉-8-基)吡啶 (dqp) 配体的双齿钌 (II) 多吡啶型配合物，并研究了它们的光物理性质。该复合物易于在具有守恒准 C2v 对称性的中心吡啶的 4 位取代，这允许扩展到无异构体的棒状分子阵列，用于电子和能量转移的矢量控制。在母体 [Ru(dqp) 2](2+) 复合体 (1) 上执行的 DFT 计算预测出比典型双齿复合体 [Ru(tpy)2](2+) 更八面体的结构（tpy 为 2,2' :6',2"-三联吡啶)由于较大的配体咬合角，X射线晶体学证实了这一点。强烈的可见吸收带，基于时间相关的 DFT 计算，最大波长为 491 nm 被指定为金属到配体电荷转移 (MLCT) 跃迁。图 1 显示了其最低激发态 ((3) MLCT) 的室温发射 (Phi = 0.02)，其寿命很长 (tau = 3 微秒)。长寿命是由于更强的配体场，因为更多的八面体结构
• Synthesis and Characterization of 2,6-Di(quinolin-8-yl)pyridines. New Ligands for Bistridentate Ru^II Complexes with Microsecond Luminescent Lifetimes
  作者：Michael Jäger、Lars Eriksson、Jonas Bergquist、Olof Johansson

  DOI：10.1021/jo7015373

  日期：2007.12.1

  The synthesis of 4-substituted and 4-aryl-substituted 2,6-di(quinolin-8-yl)pyridines is described. The tridentate ligands were prepared via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction or via a one-step ring-forming reaction generating the central pyridine ring. X-ray crystal structures and H-1 NMR shifts are discussed and compared to the corresponding data for a Ru-II bistridentate complex. Intramolecular stacking of two quinoline units in the Run complex is suggested by H-1 NMR data and also observed in the X-ray structure.