4-(4″-methoxyphenyl)-6-phenyl-2,2′-bipyridine | 171511-92-5

• 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: 4-(4″-methoxyphenyl)-6-phenyl-2,2′-bipyridine
• 英文别名: 2-(2-pyridyl)-4-(4-methoxylphenyl)-6-phenylpyridine；4-(p-methoxyphenyl)-6-phenyl-2,2'-bipyridine；4-(4-methoxyphenyl)-6-phenyl-2,2'-bipyridine；6-phenyl-4-(4-CH3OC6H4)-2,2'-bipyridine；4-(4-Methoxyphenyl)-2-phenyl-6-pyridin-2-ylpyridine
• CAS: 171511-92-5
• 化学式: C₂₃H₁₈N₂O
• 分子量: 338.409
• InChiKey: NXYQPFPMKIROKW-UHFFFAOYSA-N

物化性质

• 沸点：
  495.5±45.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 4-(4″-methoxyphenyl)-6-phenyl-2,2′-bipyridine 以 水 、 乙腈 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  6-苯基-2,2联吡啶的发光单核和双核环金属化钯（II）配合物：与铂（II）类似物的光谱和结构比较。

  摘要：

  单核环金属化Pd（II）配合物[Pd（L1）X]（HL1 = 6-苯基-2,2'-联吡啶; X = Cl，la; Br，1b; I，1c），[Pd（L1）PPh3 ] +（1d），[Pd（L2-5）Cl] [2a-5a，HL2-5 = 4-（芳基）-6-苯基-2,2'-联吡啶；芳基=苯基（2），4-氯苯基（3），4-甲苯基（4），4-甲氧基苯基（5）]和双核衍生物[Pd2（L1-5）2（mu-dppm）] 2+（1e制备-5e，dppm ＝双（二苯基膦基）甲烷）和[Pd2（L1）2（mu-dppCs）] 2 +，（1f，dppC5 ＝ 1，5-双（二苯基膦基）戊烷）。1d（ClO4），1e（ClO4）2 x DMF和2e（ClO4）2的晶体结构已通过X射线晶体学测定。Le和2e中的Pd-Pd距离的大小（分别为3.230（1）和3.320（2）A）表明金属与金属之间的相互作用最小，尽管芳香族配体的pi堆积（平面间距分别为3

  DOI：

  10.1021/ic991089g
• 作为产物：
  描述：

  4-甲氧基查耳酮 在 氨 、 苯亚甲基苯乙酮 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.17h， 生成 4-(4″-methoxyphenyl)-6-phenyl-2,2′-bipyridine
  参考文献：
  名称：

  在吡啶基官能化的吡喃鎓盐，吡啶和λ取代基效应3，σ 2 -phosphinines：一个基本系统的研究†

  摘要：

  制备了一系列取代的，吡啶基官能化的2,4,6-三芳基吡啶鎓盐，并对其光吸收和发射性质进行了研究。与P（森达反应后3）3，相应的λ 3个得到-phosphinines，其携带的4-或6-芳基环±I和±中号的取代基上。在DFT计算的支持下，对这些低坐标的P，N杂化配体的σ供体和π供体以及π受体性质进行了系统的评估。出于比较的原因，模块化合成方法使我们能够同时合成与结构相关的联吡啶衍生物。螯合配体与[W（CO）6 ]在THF中反应，得到相应的[（P ^ N）W（CO）4]和[（N ^ N）W（CO）4 ]配合物。所选配位化合物的晶体学特征表明，吡啶基次膦基化合物和联吡啶基化合物之间存在显着的结构差异。通过红外光谱对它们的表征使对各自配体的电子性质的实验见识得到了深入了解。

  DOI：

  10.1039/c8dt01441h

文献信息

• Spectroscopic Study of DNA Hydrolysis, DNA Intercalative, and Electrostatic Interaction Activity Exerted by Drug Based Coordination Compounds
  作者：Mohan N. Patel、Bhupesh S. Bhatt、Promise A. Dosi

  DOI：10.1002/zaac.201100307

  日期：2012.1

  mononuclear copper(II) complexes with second generation fluoroquinolone drug ciprofloxacin (CFL) and some bipyridine derivatives (An) of type [Cu(CFL)(An)Cl]·2H2O. The DNA binding free energies were evaluated by studying the effect of salt concentrations on DNA binding. DNA interactions were investigated by using DNA melting temperature studies, viscosity measurements, absorption titration, and gel electrophoresis

  我们的工作重点是合成和表征中性单核铜 (II) 配合物与第二代氟喹诺酮类药物环丙沙星 (CFL) 和一些 [Cu(CFL)(An)Cl]·2H2O 型联吡啶衍生物 (An)。通过研究盐浓度对 DNA 结合的影响来评估 DNA 结合自由能。通过使用 DNA 熔解温度研究、粘度测量、吸收滴定和凝胶电泳实验来研究 DNA 相互作用。还研究了超氧化物歧化酶 (SOD) 样活性（IC50 值）和金属配合物的抗菌活性。为了验证质粒 DNA 切割的正确机制途径，在自由基清除剂的存在下进行了凝胶电泳实验。
• Light-Emitting Tridentate Cyclometalated Platinum(II) Complexes Containing σ-Alkynyl Auxiliaries:  Tuning of Photo- and Electrophosphorescence
  作者：Wei Lu、Bao-Xiu Mi、Michael C. W. Chan、Zheng Hui、Chi-Ming Che、Nianyong Zhu、Shuit-Tong Lee

  DOI：10.1021/ja0317776

  日期：2004.4.1

  sigma-alkynyl ligands, the emission color of this class of platinum(II) complexes can be tuned from green-yellow to saturated red. In addition to (3)MLCT [Pt(5d) --> pi*(C/N/N)] and (3)IL(C/N/N), intriguing (3)IL(alkynyl) excited states localized on -(C[triple bond]C)(4)- and -(C[triple bond]Cpyrenyl-1) moieties that afford narrow-bandwidth emissions have been observed. Selected Pt(II) complexes were doped into

  该配合物在具有高量子产率和微秒寿命的流体和玻璃溶液中显示出良好的热稳定性和强烈的磷光。它们的发射能量对溶剂极性、环金属化和芳基乙炔基上的取代基的电子亲和力以及寡炔基配体的长度敏感。通过选择合适的环金属化和 σ-炔基配体，这类铂 (II) 配合物的发射颜色可以从绿黄色调到饱和红色。除了 (3) MLCT [Pt(5d) --> pi*(C/N/N)] 和 (3)IL(C/N/N) 之外，有趣的 (3)IL(炔基) 激发态位于-(C[三键]C)(4)-和-(C[三键]Cpyrenyl-1)部分提供窄带发射已经被观察到。将选定的 Pt(II) 配合物掺杂到多层的发射区中，气相沉积有机发光二极管。可调电致磷光能量类似于这些发射器的流体溶液中记录的能量，并且这些设备表现出高亮度和效率（高达 4.2 cd A(-1)）。
• Novel luminescent cyclometaiated and terpyridine gold(III) complexes and DNA binding studies
  作者：Heng-Qian Liu、Tsz-Chun Cheung、Shie-Ming Peng、Chi-Ming Che

  DOI：10.1039/c39950001787

  日期：——

  Two gold complexes, [AuIII4-MeOPh-(Phbipy)}Cl]·CF3SO31 and [AuIII(4-MeOPh-terpy)Cl]·(ClO4)22[4-MeOPh-(Phbipy)= 4′-(4-methoxyphenyl)-6′-phenyl-2,2′-bipyridine, 4-MeOPh-terpy = 4′-(4-methoxyphenyl)-2, 2′,6′, 2″-terpyridine] are prepared, and their interactions with calf-thymus DNA, poly(dG-dC)2and poly(dA-dT)2, investigated by spectroscopic means; in the reaction with ct DNA, 1 has a higher binding constant than 2, but the latter has a higher degree of AT specificity.

  制备了两种金配合物，[AuIII4-MeOPh-(Phbipy)}Cl]·CF3SO31和[AuIII(4-MeOPh-terpy)Cl]·(ClO4)22[4-MeOPh-(Phbipy)= 4′-(4-甲氧基苯基)-6′-苯基-2,2′-联吡啶，4-MeOPh-terpy = 4′-(4-甲氧基苯基)-2, 2′,6′, 2″-三联吡啶]，并通过光谱学方法研究了它们与牛胸腺DNA、poly(dG-dC)2和poly(dA-dT)2的相互作用；在与ct DNA的反应中，1的结合常数比2高，但后者具有更高的AT特异性。
• DNA interactions and cytotoxic studies of cis-platin analogues of substituted 2,2′-bipyridines
  作者：Mohan N. Patel、Pradhuman A. Parmar、Deepen S. Gandhi、Anshul P. Patidar

  DOI：10.1016/j.saa.2012.05.043

  日期：2012.11

  Platinum(II) complexes [Pt(4 ''-fpbpy)Cl-2] (1), [Pt(4 ''-mepbpy)Cl-2] (2), [Pt(4 ''-mpbpy)Cl-2] (3) and [Pt(4 ''-bopbpy)Cl-2] (4) where 4 ''-fpbpy = 4-(4 ''-fluorophenyl)-6-phenyl-2,2'-bipyridine, 4 ''-mepbpy = 4-(4 ''-methylphenyl)-6-phenyl-2,2'-bipyridine, 4 ''-mpbpy = 4-(4 ''-methoxyphenyl)-6-phenyl-2,2'-bipyridine, 4 ''-bopbpy = 4-(4 ''-benzyloxyphenyl)-6-phenyl-2,2'-bipyridine} have been synthesized and characterized. The binding strength and binding mode of the complexes with HS DNA (Herring Sperm) have been investigated by absorption titration and viscosity measurement studies. The results have been revealed that the complexes bind to DNA by covalent mode with intrinsic binding constant K-b ranging from 6.05 x 10(4) M-1 to 3.48 x 10(5) M-1. The unwinding angle of pUC19 DNA has been evaluated by gel electrophoresis assay. The brine shrimp bioassay has been performed to study the in vitro cytotoxic properties of the synthesized metal complexes. (C) 2012 Elsevier B.V. All rights reserved.
• Probing d⁸−d⁸ Interactions in Luminescent Mono- and Binuclear Cyclometalated Platinum(II) Complexes of 6-Phenyl-2,2‘-bipyridines
  作者：Siu-Wai Lai、Michael Chi-Wang Chan、Tsz-Chun Cheung、Shie-Ming Peng、Chi-Ming Che

  DOI：10.1021/ic990238s

  日期：1999.9.1

  A series of luminescent mono- and binuclear cyclometalated platinum(II) complexes, namely [Pt(L1-6)Cl] (1a-6a; HL1-6 = 4-(aryl)-6-phenyl-2,2'-bipyridine; aryl = H (1), phenyl (2), 4-chlorophenyl (3), 4-tolyl (4), 4-methoxyphenyl (5), 3,4,5-trimethoxyphenyl (6)), [Pt(L-1)E](+) (E = py (7), PPh3 (8)), [Pt-2(L1-6)(2)(mu-dppm)](2+) (1b-6b, dppm = bis(diphenylpbosphino)methane), [Pt-2(L-1)(2)(mu-pz)](+) (9, Hpz = pyrazole), and [Pt-2(L-1)(2)(mu-dppcC(n))](2+) (dppC(n) = bis(diphenylphosphino)propane (10, n = 3) and -pentane (11, n = 5)), were synthesized in order to examine fluid- and solid-state oligomeric d(8)-d(8) and ligand-ligand interactions. The molecular structures of 4b(ClO4)(2) and 9(PF6) reveal intramolecular Pt-Pt distances of 3.245(1) and 3.612(2) Angstrom, respectively. While minimal metal-metal communication is expected for 9, weak pi-pi interactions are possible. All complexes described in this work are emissive in fluid solution at room temperature. Negligible changes in emission energy are detected by incorporating different aryl substituents into the 4-position of 6-phenyl-2,2'-bipyridine, and this indicates little electronic delocalization between them. Self-quenching of the (MLCT)-M-3 emission by the mononuclear derivatives are observed in CH2Cl2 at 298 K, and a red shia in the emission energy is exhibited by complex 7 in acetonitrile at 77 K. The fluid emissions of the mu-dppm species 1b-6b at lambda(max) 652-662 nm appear at substantially lower energies than their mononuclear counterparts and show dramatic solvatochromic effects. These emissions are ascribed to (3)[d sigma*, pi*] excited states. In contrast, the emission of 10 and 11, bearing long bridging diphosphine ligands, are attributed to (MLCT)-M-3 states of non-interacting [Pt(L-1)] moieties. Significantly, the luminescence of the mu-pyrazolate complex 9 displays transitional features which are reminiscent of both (3)[d sigma*, pi*] and (MLCT)-M-3 excited states. Hence a relationship is observed between emission energy, the nature of the lowest energy excited state, and metal-metal interactions. The excited-state redox potential [E(*Pt-2(2+)/Pt-2(+))] of 1b has been estimated by electrochemical studies (1.61 V vs NHE) and by quenching experiments with aromatic hydrocarbons (1.63 V vs NHE).