p-pyridyl ferrocene | 120577-85-7

• 英文名称: p-pyridyl ferrocene
• 英文别名: ferrocenyl-4-pyridine；4-ferrocenylpyridine；4-pyridyl ferrocene；4-FcPyr；[Fe(η5-C5H4-4-C5H4N)(η5-C5H5)]
• CAS: 120577-85-7
• 化学式: C₁₅H₁₃FeN
• 分子量: 263.122
• InChiKey: RSUROXOCTIRTSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  mono(pentaamino(hydroxy)ruthenium(VIII)) mono(hexafluorophosphate(V)) hydrate 、 p-pyridyl ferrocene 以 丙酮 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Solvent-Dependent Studies of Intervalence Transfer of Mixed-Valence Complexes Containing Ferrocenylpyridine and Rutheniumammines

  摘要：

  Two heterobimetallic complexes of [Fc(4-Py)Ru(NH3)(5)](PF6)(2) (1) and [Fc(3-Py)Ru(NH3)(5)](PF6)(2) (2) (Fc(4-Py) = 4-ferrocenylpyridine, Fc(3-Py) = 3-ferrocenylpyridine) have been synthesized and characterized for the purpose of investigating optical and thermal electron transfer. The mixed-valence species generated in situ using ferrocenium hexafluorophosphate as the oxidant show Robin and Day class II behavior, and the oxidized sites are ruthenium centered, Delta E(1/2)degrees, E(1/2)degrees(Fe-III/Fe-II) - E(1/2)degrees(Ru-III/Ru-II), an estimate of Delta E-o that is an energetic difference between the donor and acceptor sites, changes sharply with variation of solvents. Good linear relationship exists between Delta E(1/2)degrees and Gutmann solvent donor number (DN) and Delta E(1/2)degrees versus DN plots yield a slope of 20.4 +/- 1.6 mV/DN for [Fc(4-Py)Ru(NH3)(5)](2+/3+/4+) and a slope of 21.1 +/- 2.2 mV/DN for [Fc(3-Py)Ru(NH3)(5)](2+/3+/4+). The solvent-dependent IT bands were found to vary almost exclusively with Delta E(1/2)degrees. The continuum dielectric approximation is found to be adequate, and the (E-op - Delta E-o) versus (1/epsilon(op) - 1/epsilon(s)) plot yields a straight line with a slope of 3848 +/- 1444 and an intercept of 4265 +/- 227 cm(-1) for [Fc(4-Py)Ru(NH3)(5)](3+). The corresponding values for [Fc(3-Py)Ru(NH3)(5)](3+) are 2328 +/- 1560 and 6712 +/- 100 cm(-1). The thermal electron transfer (the reverse of the optical process, viz., Ru-II --> Fe-III electron transfer) is adiabatic for [FC(4-Py)Ru(NH3)(5)](3+) but somewhat nonadiabatic (kappa approximate to 0.6) for [Fc(3-Py)Ru(NH3)(5)](3+). The thermal transfer rate constants of both complexes decrease exponentially with increasing solvent donor number and show close magnitude in all solvents despite [Fc(3-Py)Ru(NH3)(5)](3+) having apparently a shorter through-space distance and lower activation energies. However, these calculated k(th) values should be used with caution because no experimental data as measured by flash photolysis techniques are available.

  DOI：

  10.1021/ic9713341
• 作为产物：
  描述：

  4-溴吡啶 、 ferrocenylmagnesium bromide 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 为溶剂， 以82%的产率得到p-pyridyl ferrocene
  参考文献：
  名称：

  Miller, Timothy M.; Ahmed, Kazi J.; Wrighton, Mark S., Inorganic Chemistry, 1989, vol. 28, # 12, p. 2347 - 2355

  摘要：

  DOI：

文献信息

• Ferrocenyl-nitrogen donor ligands. Synthesis and characterization of rhodium(I) complexes of ferrocenylpyridine and related ligands
  作者：Jaisheila Rajput、Alan T. Hutton、John R. Moss、Hong Su、Christopher Imrie

  DOI：10.1016/j.jorganchem.2006.05.048

  日期：2006.11

  preparation of a series of complexes of the types [RhCl(CO)2(L)], [RhCl(cod)(L)] and [Rh(cod)(L)2]ClO4, where L is a ligand incorporating a ferrocenyl group and a pyridine ring is described. Complexes were characterized using NMR, IR and electronic spectroscopy. The electrochemical behaviour of the complexes was examined using cyclic voltammetry. The X-ray structures of three of the complexes, [RhCl(CO)2NC5

  [RhCl（CO）2（L）]，[RhCl（cod）（L）]和[Rh（cod）（L）2 ] ClO 4类型的一系列配合物的制备，其中L是掺入的配体描述了二茂铁基和吡啶环。使用NMR，IR和电子光谱对复合物进行表征。使用循环伏安法检查复合物的电化学行为。3复合物的X-射线结构，[的RhCl（CO）2 NC 5 H ^ 4 CNC 6 ħ 4（η 5 -C 5 H ^ 4）的Fe（η 5 -C 5 H ^ 5）}]，[RhCl（鳕鱼）（3-Fcpy）]和[RhCl（鳕鱼）3-Fc（C 6 H 4）py}]被确定。
• Regulating the anticancer properties of organometallic dendrimers using pyridylferrocene entities: synthesis, cytotoxicity and DNA binding studies
  作者：Preshendren Govender、Tina Riedel、Paul J. Dyson、Gregory S. Smith

  DOI：10.1039/c6dt00849f

  日期：——

  A new series of eight first- and second-generation heterometallic ferrocenyl-derived metal–arene metallodendrimers, containing ruthenium(II)–p-cymene, ruthenium(II)–hexamethylbenzene, rhodium(III)–cyclopentadienyl or iridium(III)–cyclopentadienyl moieties have been prepared. The metallodendrimers were synthesized by first reacting DAB-(NH2)n (where n = 4 or 8, DAB = diaminobutane) with salicylaldehyde

  新的八种第一和第二代杂金属二茂铁基衍生的金属-芳烃金属树枝状化合物，包含钌（II）-对-异丙基，钌（II）-六甲基苯，铑（III）-环戊二烯基或铱（III）-环戊二烯基部分已经准备好了。首先通过使DAB-（NH 2）n（n = 4或8，DAB =二氨基丁烷）与水杨醛反应，然后再使席夫碱树状配体与适当的[[ η 6 - p -iPrC 6 ħ 4 Me）中的RuCl2 ] 2，[（η 6 -C 6我6）的RuCl 2 ] 2，[（η 5 -C 5我5）的IrCl 2 ] 2或[（η 5 -C 5我5）的RhCl 2 ] 2二聚体，在4-吡啶基二茂铁的存在下。杂金属双核类似物被制备为较大的金属树枝状大分子的模型。所有络合物均已使用分析和光谱法进行了表征。评估了异金属金属树枝状大分子及其双核类似物对A2780顺铂敏感和A2780cisR顺铂耐药的人卵巢癌细胞系以及对非致瘤性HEK-293人胚胎肾
• Activation by Oxidation: Ferrocene-Functionalized Ru(II)-Arene Complexes with Anticancer, Antibacterial, and Antioxidant Properties
  作者：Changhua Mu、Kathleen E. Prosser、Shane Harrypersad、Gregory A. MacNeil、Rikesh Panchmatia、John R. Thompson、Soumalya Sinha、Jeffrey J. Warren、Charles J. Walsby

  DOI：10.1021/acs.inorgchem.8b02542

  日期：2018.12.17

  Organometallic Ru(II)-cymene complexes linked to ferrocene (Fc) via nitrogen heterocycles have been synthesized and studied as cytotoxic agents. These compounds are analogues of Ru(II)-arene piano-stool anticancer complexes such as RAPTA-C. The Ru center was coordinated by pyridine, imidazole, and piperidine with 0-, 1-, or 2-carbon bridges to Fc to give six bimetallic, dinuclear compounds, and the

  合成并研究了通过氮杂环与二茂铁（Fc）连接的有机金属Ru（II）-月桂烯复合物，并作为细胞毒性剂进行了研究。这些化合物是Ru（II）-芳烃钢琴凳式抗癌复合物（如RAPTA-C）的类似物。Ru中心通过吡啶，咪唑和哌啶与Fc的0、1，或2碳桥键配位得到六种双金属双核化合物，并将这些配合物的性质与其未Fc官能化的母体进行了比较化合物。确定了其中五个化合物，其Ru-cymene母体化合物和一种不寻常的三核化合物的晶体结构。循环伏安法用于测定正式的M III / IIRu-cymene-Fc配合物的每个金属中心的电势，在每种情况下均观察到不同的单电子波。发现Fc-官能化的复合物对HT29人结肠腺癌细胞显示出良好的细胞毒性，而母体化合物是无活性的。同样，Ru-cymene-Fc化合物对枯草芽孢杆菌具有抗菌活性，而未官能化的复合物则没有。在这两种情况下，IC 50值都与Fc + / 0定量相关还原潜力。
• Ferrocene donor linked to pyridine/pyridinium acceptor <i>via</i> a systematically enlarged π-linker
  作者：Jiří Kulhánek、Milan Klikar、Oldřich Pytela、Zdenka Růžičková、Filip Bureš

  DOI：10.1039/d1ra08186a

  日期：——

  Nine chromophores with ferrocene donor and pyridine/pyridinium acceptors have been prepared and further investigated.

  已经准备并进一步研究了具有二茂铁供体和吡啶/吡啶盐受体的九个色团。
• Synthesis, characterization and cytotoxicity of some palladium(II), platinum(II), rhodium(I) and iridium(I) complexes of ferrocenylpyridine and related ligands. Crystal and molecular structure of trans-dichlorobis(3-ferrocenylpyridine)palladium(II)
  作者：Jaisheila Rajput、John R Moss、Alan T Hutton、Denver T Hendricks、Catherine E Arendse、Christopher Imrie

  DOI：10.1016/j.jorganchem.2004.01.034

  日期：2004.5

  Coordination studies of the substituted pyridines (L) were carried out with platinum, palladium, rhodium and iridium. This resulted in the preparation of the following types of complexes: [MCl(CO)2(L)] and [M(cod)(L)2]ClO4 where M=Rh or Ir, cod=1,5-cyclooctadiene; [M′Cl2(L)2] where M′=Pt or Pd. The X-ray crystal structure of trans-dichlorobis(3-ferrocenylpyridine)palladium was obtained. The complexes were screened

  一系列二茂铁氮供体配体，包括ferrocenylpyridines，ferrocenylphenylpyridines和1,1-的制备' -二（2-吡啶基）二茂铁进行说明。用铂，钯，铑和铱对取代的吡啶（L）进行配位研究。这导致制备以下类型的配合物：[MCl（CO）2（L）]和[M（cod）（L）2 ] ClO 4，其中M ＝ Rh或Ir，cod ＝ 1，5-环辛二烯； n ＝ 1。[M '氯2（L）2 ]，其中M ' = Pt或Pd。反式的X射线晶体结构获得了-二氯双（3-二茂铁基吡啶）钯。筛选复合物针对两种人类癌细胞系的活性。至少两种复合物显示出与广泛使用的化学治疗剂顺铂相似的生长抑制作用。