5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine

• 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: 5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine
• 英文别名: 5-Phenyl-2,8-dipyridin-2-ylpyrido[2,3-b][1,8]naphthyridine；5-phenyl-2,8-dipyridin-2-ylpyrido[2,3-b][1,8]naphthyridine
• 化学式: C₂₇H₁₇N₅
• 分子量: 411.465
• InChiKey: APWAHQCQYHDMLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine 在 ascorbic acid 、 lithium chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  New Series of Dinuclear Ruthenium(II) Complexes Synthesized Using Photoisomerization for Efficient Water Oxidation Catalysis

  摘要：

  A new series of proximal proximal-[Ru-2(tpy)(2)(L)XY](n+) (p,p-Ru2XY, tpy = 2,2':6',2 ''-terpyridine, L = 5-phenyl-2,8-di(2-pyridyl)-1,9,10-anthyridine, X and Y = other coordination sites) were synthesized using, photoisomerization of a mononuclear complex. The p,p-Ru2XY complexes undergo unusual reversible bridge-exchange reactions to generate p,p-Ru-2(mu-Cl), p,p-Ru-2(mu-OH), and p,p-Ru-2(OH)(OH2) with mu-Cl, mu-OH, as well as hydroxo and aquo ligands at X and Y sites of p,p-Ru2XY, respectively. The geometric and electronic structures of these complexes were characterized based on UV vis and H-1 NMR spectra, X-ray crystallography, and density functional theory (DFT) calculations. H-1 NMR data showed C-2 symmetry of p,p-Ru-2(OH)(OH2) with the distorted L chelate and nonequivalence of two tpy ligands, in contrast to the C-2 symmetry of p,p-Ru-2(mu-Cl) and p,p-Ru-2(mu-OH). However, irrespective of the lower symmetry, p,p-Ru-2(OH)(OH2) is predominantly formed in neutral and weakly basic conditions due to the specially stabilized core structure by multiple hydrogen-bond interactions among aquo, hydroxo, and backbone L ligands. The electrochemical data suggested that p,p-Ru-2(OH)(OH2) (Ru-II-OH:Ru-II-OH2) is oxidized to the Ru-III-OH:Ru-III-OH state at 0.64 V vs saturated calomel electrode (SCE) and further to Ru-IV=O:Ru-IV-OH at 0.79 V by successive 1-proton-coupled 2-electron processes at pH 7.0. The cyclic voltammogram data exhibited that the p,p-Ru-2(OH)(OH2) complex works more efficiently for electrocatalytic water oxidation, compared with a similar mononuclear complex distal-[Ru(tpy)(L)OH2](2+) (d-RuOH2) and p,p-Ru-2(mu-Cl) and p,p-Ru-2(mu-OH), showing that the p,p-Ru-2 core structure with aquo and hydroxo ligands is important for efficient electrocatalytic water oxidation. Bulk electrolysis of the p,p-Ru-2(OH)(OH2) solution corroborated the electrocatalytic cycle involving the Ru-III-OH:Ru-III-OH state species as a resting state. The mechanistic insight into O-O bond formation for O-2 production was provided by the isotope effect on electrocatalytic water oxidation by p,p-Ru-2(OH)(OH2) and d-RuOH2 in H2O and D2O media.

  DOI：

  10.1021/acs.inorgchem.5b01264
• 作为产物：
  描述：

  2,6-diamino-4-phenylpyridine-3,5-dicarbonitrile 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine
  参考文献：
  名称：

  Synthesis of heterocyclic compounds containing three contiguous hydrogen bonding sites in all possible arrangements

  摘要：

  The synthesis of compounds containing three contiguous hydrogen bond sites is reported. There are six ways of arranging three adjacent hydrogen bond donor (D) and acceptor (A) sites. General synthetic routes to heterocyclic compounds with each arrangement is reported.

  DOI：

  10.1016/0040-4020(94)00922-h
• 作为试剂：
  描述：

  、 三苯基膦 在 5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以95%的产率得到
  参考文献：
  名称：

  基于 Anthyridine 的五氮供体通过 Pd(II) 离子从单齿切换到四齿

  摘要：

  在银盐的存在下，用 (PPh 3 ) 2 PdCl 2或 (dppe)PdCl 2处理 5-苯基-2,8-双(2-吡啶基) 蒽 ( L )导致形成 [反式- ( PPh 3 ) 2 Pd L Cl](BF 4 ) ( 1a ), [ trans- (PPh 3 ) 2 Pd L (MeCN)](BF 4 ) 2 ( 1b ), [ trans- (PPh 3 ) 2 Pd L Cl ](PF 6 ) (1c )，或[顺式- (dppe)Pd L Cl](BF 4 ) ( 4 )。这些配合物中的配体L充当单齿配体，其中 N (10)的蒽啶与金属中心结合。在PPh 3存在下，双核配合物[Pd 2 L (CH 3 CN) 2 Cl 2 ](BF 4 ) 2 ( 2 ) 和[Pd 2 L (CH 3 CN) 4 ](BF 4 ) 4 ( 3 )) 容易地进行去螯合，分别产生1a , b，而2与 d

  DOI：

  10.1021/acs.organomet.1c00569

文献信息

• Hetero-Bimetallic Complexes Based on an Anthyridine Ligand Preparation and Catalytic Activity
  作者：Shih-Chieh Aaron Lin、Yi-Hung Liu、Shie-Ming Peng、Shiuh-Tzung Liu

  DOI：10.1021/acs.organomet.9b00682

  日期：2020.1.13

  confirmed by X-ray crystallography. Complex Ru–Pd exhibits catalytic activities for the tandem reactions of Suzuki–Miyaura coupling/transfer hydrogenation of p-bromoacetophenone with phenylboronic acid in isopropanol, whereas Ir–Pd shows a moderate activity. However, complex Rh–Pd does not behave the same way. Furthermore, catalytic activity of these heterobimetallic complexes toward debromination/transfer

  基于anthyridine -配体络合大号与[（η 6 -cymene）的RuCl 2 ] 2，混合[Cp *的RhCl 2 ] 2，和混合[Cp *的IrCl 2 ] 2，得到的单核络合物：[（Ñ，ñ -大号）钌（η 6 -cymene）CL]氯（1），[（ñ，ñ -大号）的Rh（CP *）CL]氯（2），和[（ñ，N-大号）IR（CP *）CL]氯（3）分别[ L＝ 5-苯基-2，8-二-2-吡啶基吡啶并吡啶]。在与（CH治疗3 CN）的PdCl 2复合物，1 - 3后行邻金属化，得到双核配合物的Ru-钯，铑-钯，和铱-钯，分别。配合物均通过光谱法表征，某些配合物通过X射线晶体学进一步证实。复杂的Ru-Pd在Suzuki-Miyaura的对接反应/对溴苯乙酮与苯硼酸在异丙醇中的转移氢化反应中表现出催化活性，而Ir-Pd则表现出中等活性。但是，复杂Rh–Pd的行为不同。此外，朝向的脱溴/
• Diruthenium complex catalyzed reduction of nitroarenes-investigation of reaction pathway
  作者：Shih-Chieh Aaron Lin、Yi-Hung Liu、Shie-Ming Peng、Shiuh-Tzung Liu

  DOI：10.1016/j.mcat.2019.01.005

  日期：2019.4

  A diruthenium complex, [(L)Ru2(η6-C6H6)2Cl2](PF6)2 (1) (L = 5-phenyl-2,8-di-2-pyridinylanthyridine), was prepared and characterized. This diruthenium complex 1 was found to be an efficient catalyst for the reduction of aromatic nitro compounds leading to the corresponding aniline derivatives with the use of hydrazine as the reducing agent at 80 °C in an ethanol solution. Catalytic activity of 1 towards

  甲二钌络合物，[（大号）的Ru 2（η 6 -C 6 H ^ 6）2氯2 ]（PF 6）2（1）（L = 5-苯基-2,8-二-2- pyridinylanthyridine），是准备和表征。发现该二钌络合物1是在乙醇溶液中在80℃下使用肼作为还原剂还原芳族硝基化合物以产生相应的苯胺衍生物的有效催化剂。催化活性为1研究了各种可能导致苯胺中间体的方法，以了解其反应途径。这些研究表明，这种还原反应是通过直接途径进行的，羟胺是主要的中间体，随后在催化条件下出现了苯胺，证明了这一点。因此，讨论了该催化体系的反应途径。
• Tetra- and Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity
  作者：Shih-Chieh Aaron Lin、Bo-Kai Su、Yi-Hung Liu、Shie-Ming Peng、Shiuh-Tzung Liu

  DOI：10.1021/acs.organomet.1c00226

  日期：2021.7.12

  manipulation of stoichiometric ratio of ligand to metal precursor. The catalytic activity of these complexes for carbonylative Suzuki–Miyaura cross-coupling was investigated. Complex 2 shows an excellent catalytic activity on the reaction of aryl iodide with arylboronic acid in the presence of atmospheric pressure of CO to give the corresponding benzophenones.

  的络合大号[大号= 5-苯基-2,8-二-2-吡啶基- anthyridine]与[将Pd（CH 3 CN）4 ]（BF 4）2和[加入Pd（CH 3 CN）3 CL]（BF 4 ) 以 1:2 的摩尔比呈现相应的双核配合物 [Pd 2 L (CH 3 CN) 4 ](BF 4 ) 4 ( 1 ) 和 [Pd 2 L (CH 3 CN) 2 Cl 2 ](BF 4 ) 2 ( 2）， 分别。然而，用(COD)PdCl 2处理L，然后进行阴离子交换产生四核复合物[Pd 4 L 3 Cl 4 ](PF 6 ) 4 ( 4a )。这些配合物的结构由光谱学和 X 射线晶体学表征。通过操纵配体与金属前体的化学计量比来研究这三种配合物的相互转化。研究了这些配合物对羰基化 Suzuki-Miyaura 交叉偶联的催化活性。复合体2 在常压 CO 存在下，芳基碘与芳基硼酸反应生成相应的二苯甲酮显示出优异的催化活性。
• Dinickel complexes with anthyridine-based ligands
  作者：Da-Wei Huang、Yi-Hung Liu、Shie-Ming Peng、Shiuh-Tzung Liu

  DOI：10.1039/c6dt00567e

  日期：——

  new dinickel complexes with anthyridine-based ligands, 5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine (L2) and 5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine (L3), are reported. Complexation of Ni(OAc)2 with L2 and L3 in trifluoroacetic acid provided the corresponding dinickel complexes [Ni2(L2)(H2O)6(CF3COO)2}(CF3COO)2] (2) and [Ni2(L3)(CF3COO)4(H2O)] (3), respectively. Both complexes were

  具有基于蒽的配体的两个新的二镍配合物，5-苯基-2,8-双（2-吡啶基）-1,9,10-蒽（L 2）和5-苯基-2,8-双（6'-据报道有联吡啶基）-1,9,10-蒽啶（L 3）。Ni（OAc）2与L 2和L 3在三氟乙酸中的络合提供了相应的二镍配合物[Ni 2（L 2）（H 2 O）6（CF 3 COO）2 }（CF 3 COO）2 ]（2）和[Ni 2（L 3）（CF 3 COO）4（H 2 O）]（3）。两种配合物均通过光谱学方法表征，并通过X射线晶体学进一步证实。2和3的结构分析表明，配合物中的Ni⋯Ni距离分别为5.4086（6）和5.0138（7）Å。评价了配合物2和3对羧酸还原的催化活性。看来配合物3显示出对二苯基硅烷将羧酸盐还原成相应的醇具有良好的催化活性。
• Ruthenium Complexes with an Anthyridine‐based Ligand. Synthesis, Characterization and Catalytic Activity
  作者：Ying‐Hao Lo、Yi‐Hung Liu、Shie‐Ming Peng、Shiuh‐Tzung Liu

  DOI：10.1002/jccs.201300084

  日期：2013.7

  Complexation of 2,7‐bis(2‐pyridinyl)‐9‐phenylanthyridine (4) with [RuCl2(CO)3(THF)] and [(η6‐p‐cymene)RuCl2]2 provided the mono‐nuclear complex [(4)Ru(CO)3Cl][RuCl3(CO)3] (5) and the dinuclear complex [(4)Ru2(p‐cymene)2Cl2] (6), respectively. Both complexes have been characterized by spectroscopic, elemental and crystallographic analyses. Complex 6 is an efficient catalyst for the oxidative cyanation of various

  的2,7-双（2-吡啶基）络合-9- phenylanthyridine（4）配有将[RuCl 2（CO）3（THF）]和[（η 6 - p -cymene）的RuCl 2 ] 2提供的单核络合物[（4）Ru（CO）3 Cl] [RuCl 3（CO）3 ]（5）和双核络合物[（4 Ru 2（p- cymene）2 Cl 2 ]（6）。两种配合物均已通过光谱，元素和晶体学分析表征。复杂6 是各种叔芳基胺氧化氰化的有效催化剂。