4-(4-chlorophenyl)-6-phenyl-2,2'-bipyridine | 176099-70-0

• 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-chlorophenyl)-6-phenyl-2,2'-bipyridine
• 英文别名: 4-(p-chlorophenyl)-6-phenyl-2,2'-bipyridine；6-phenyl-4-(4-ClC6H4)-2,2'-bipyridine；4-(4-chlorophenyl)-2-phenyl-6-pyridin-2-ylpyridine
• CAS: 176099-70-0
• 化学式: C₂₂H₁₅ClN₂
• 分子量: 342.827
• InChiKey: GUXGDEPWJYPJEC-UHFFFAOYSA-N

物化性质

• 沸点：
  487.7±40.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  potassium tetrachloropalladate(II) 、 4-(4-chlorophenyl)-6-phenyl-2,2'-bipyridine 以 水 、 乙腈 为溶剂， 以67%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：

  2-乙酰基吡啶 在 ammonium acetate 、 碘 作用下， 以 甲醇 为溶剂， 生成 4-(4-chlorophenyl)-6-phenyl-2,2'-bipyridine
  参考文献：
  名称：

  铂 (II) 联吡啶配合物的合成、表征、共价结合和解旋度

  摘要：

  配合物 [Pt(3''-clpbpy)Cl2] (1) [3''-clpbpy = 4-(3''-chlorophenyl)-6-phenyl-2, 2'-bipyridine], [Pt(4' '-clpbpy)Cl2] (2) [4''-clpbpy = 4-(4''-氯苯基)-6-苯基-2, 2'-联吡啶], [Pt(3''-brpbpy)Cl2] ( 3) [3''-brpbpy = 4-(3''-溴苯基)-6-苯基-2, 2'-联吡啶]和[Pt(4''-brpbpy)Cl2] (4) [4'' -brpbpy = 4-(4''-bromophenyl)-6-phenyl-2, 2'-bipyridine] 合成并表征。通过吸收滴定和粘度测量研究了复合物与鲱鱼精子 DNA (HS DNA) 的结合。发现复合物具有以共价方式与DNA相互作用的能力。与 HS DNA 复合物的内在结合常数

  DOI：

  10.1002/zaac.201100466

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)）。
• DNA interactions and promotion in antibacterial activities of the norfloxacin drug due to formation of mixed-ligand copper(II) complexes
  作者：Mohan N. Patel、Anshul P. Patidar

  DOI：10.1007/s00706-013-1086-4

  日期：2014.2

  mononuclear copper(II) complexes with the antibacterial drug norfloxacin in the presence of nitrogen donor heterocyclic (bipyridines) ligands were synthesized and characterized by elemental analysis, magnetic moment measurement, thermal analysis (TG), IR, LC–MS, and electronic spectra. The complexes were tested against selective gram-positive and -negative organisms for antibacterial activity. DNA binding

  摘要在氮供体杂环（联吡啶）配体存在下，合成了新型中性单核铜（II）与抗菌药诺氟沙星的复合物，并通过元素分析，磁矩测量，热分析（TG），IR，LC-MS和电子学表征光谱。测试了复合物对选择性革兰氏阳性和阴性菌的抗菌活性。使用粘度测量和吸收滴定进行了DNA结合研究。为了比较合成的铜（II）配合物在不同配体环境中的切割效率，使用超螺旋双链DNA质粒进行了DNA切割实验。在非酶系统下，积极寻求超氧化物歧化酶模拟行为用于临床和机械目的，并发现其具有良好的抗氧化活性。类似于盐水虾生物测定法，分析了合成复合物的体外细胞毒性。 图形概要
• 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).
• Interaction of palladium(II) coordination compounds with calf thymus DNA and their antibacterial activity
  作者：Mohan N. Patel、Promise A. Dosi、Bhupesh S. Bhatt

  DOI：10.1016/j.inoche.2012.04.011

  日期：2012.7

  The palladium(II) complexes of the formulations [Pd(clpbpy)Cl-2], [Pd(clcpbpy)Cl-2], [Pd(brcpbpy)Cl-2], [Pd(clmpbpy)Cl-2] clpbpy=4-(4-chlorophenyl)-6-phenyl-2,2'-bipyridine (L-1), clcpbpy=4,6-bis(4-chlorophenyl)-2,2'-bipyridine (L-2), brcpbpy=4-(4-bromophenyl)-6-(4-chlorophenyl)-2,2'-bipyridine (L-3) and clmpbpy=6-(4-chlorophenyl)-4-p-tolyl-2,2'-bipyridine (L-4)} have been synthesized and characterized using elemental analysis, electronic spectra. IR and mass spectra. The study on the interaction of the palladium complexes with calf thymus DNA (CT DNA) has been performed using absorption titration, viscosity measurements and thermal denaturation techniques. The study suggests the intercalative mode of DNA binding. Gel electrophoresis assay demonstrates the ability of the complexes to cleave the pUC19 DNA. The antibacterial activity of complexes has been screened against two Gram((+ve)) and three Gram((-ve)) microorganisms. (C) 2012 Elsevier B.V. All rights reserved.