([bis(2-pyridyl)amino]carbonyl)ferrocene | 1160162-32-2

• 英文名称: ([bis(2-pyridyl)amino]carbonyl)ferrocene
• 英文别名: [(bis(2-pyridyl)amino)carbonyl]ferrocene；[[bis(2-pyridyl)amino]carbonyl]ferrocene；[(η5-C5H5)Fe(η5-C5H4)CO(dipyridylamine)]
• CAS: 1160162-32-2
• 化学式: C₂₁H₁₇FeN₃O
• 分子量: 383.232
• InChiKey: ZDSMTESJFVCCMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 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：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) hexafluorophosphate 、 ([bis(2-pyridyl)amino]carbonyl)ferrocene 以 二氯甲烷 为溶剂， 以74%的产率得到[(η5-C5H5)Fe(η5-C5H4)CON(C5H4N)2)Cu(MeCN)2][PF6]
  参考文献：
  名称：

  Silver(I) and copper(I) complexes with ferrocenyl ligands bearing imidazole or pyridyl substituents

  摘要：

  The reactions between five ferrocenyl derivatives containing both a C=O and at least an imidazole or pyridine nitrogen atom and AgPF6, AgOTf, or [Cu(NCCH3)(4)]PF6 precursors were studied. The ligand {[bis(2-pyridyl)amino]carbonyl} ferrocene (L3), derived from (2-pyridyl)amine, favored tetrahedral coordination of Ag+ (with two ligands) and of Cu+ (with two acetonitrile ligands left from the precursor). In all the other ligands, both metal centers coordinated linearly to two ligands, preferring the imidazole or pyridinic nitrogen to other nitrogen atoms (amine) or oxygen donors.When the counter anions were triflate, the crystal structure showed a dimerization of the complex, with the ferrocenyl moieties occupying cis positions, by means of a weak Ag center dot center dot center dot Ag interaction. This was shown experimentally in the crystal structure of complex [Ag(L1)(2)]OTf (L1 = ferrocenyl imidazole) and in the presence of peaks corresponding to {Ag-2(L-2)(3)(OTf)}(+) and {Ag-2(L-2)(4)(OTf)}(+) in the mass spectra of [Ag(L-2)(2)]OTf (L2 = ferrocenyl benzimidazole). In all complexes containing PF6, there was no evidence for dimerization. Indeed, in the crystal structure of [Ag(L-2)(2)]PF6, the ferrocenyl moieties occupy trans positions and the metal centers are far from each other. DFT calculations showed that the energy of the cis and trans conformers is practically the same and the balance of crystal packing forces leads to dimerization when triflate is present. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.11.013
• 作为产物：
  描述：

  2,2'-二吡啶胺 、 ferrocenoyl chloride 在 Et₃N 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到([bis(2-pyridyl)amino]carbonyl)ferrocene
  参考文献：
  名称：

  具有单和双{[双（2-吡啶基）氨基]羰基}二茂铁配体的金属配合物

  摘要：

  配体{[双（2-吡啶基）氨基]羰基}二茂铁（L1）和1,1'-双{[双（2-吡啶基）氨基]羰基}二茂铁（L2）已经通过处理单-或 1,1'-双（氯羰基）二茂铁衍生物与二吡啶胺的比例分别为 1:1 或 1:2。已经研究了这些化合物对第 11 族和钯配合物的配体性质。配体 L1 与这些化合物配位，得到四配位 [Cu(L1)2]+、[PdCl2(L1)] 和 [Ag(OTf)(L1)(PR3)] 或三配位 [Ag(OTf)(L1) )] 和 [Au(C6F5)(L1)] 化合物。在所有情况下，配体以螯合方式配位。L2 的反应性有些不同，因为与铜或银原子的配位可以通过来自不同环戊二烯基环的几个吡啶单元发生，如 [Cu(L2)]+、[Ag2(OTf)2(L2)] 和 [Ag (OTf)(L2)(PPh3)], 或来自相同的环戊二烯基环，如 [Ag2(OTf)2(L2)(PPh3)2]。在 [Au4(C6F5)4(L2)]

  DOI：

  10.1002/ejic.200800286

文献信息

• Electrochemical studies and potential anticancer activity in ferrocene derivatives
  作者：Sara Realista、Susana Quintal、Paulo N. Martinho、Ana I. Melato、Adrià Gil、Teresa Esteves、Maria de Deus Carvalho、Liliana P. Ferreira、Pedro D. Vaz、Maria José Calhorda

  DOI：10.1080/00958972.2016.1257125

  日期：2017.1.17

  backbone, displayed slightly higher values (~11 μM). Cyclic voltammetry studies show that while the non-cytotoxic ferrocene derivatives 1, 2, and 5 follow a ferrocene-based redox behavior, derivatives 3, 4, 6, and 7 exhibit a more complex mechanism. These complex mechanisms are consistent with a more effective cytotoxic activity. Mössbauer spectroscopy parameters reflect a very small influence of the substituents

  摘要 合成了几种二茂铁衍生物（五个单核和两个双核），包括新的 N-（对氯苯基）-甲酰氨基二茂铁 (1)，并研究了它们的抗癌活性。其中带有苯并咪唑主链的 3 和 7 两种对 HeLa 细胞最有活性，IC50 值达到~5 μM，4 种带有联吡啶胺配体（~6 μM）。同样具有苯并咪唑骨架的复合物 6 显示出略高的值 (~11 μM)。循环伏安法研究表明，虽然非细胞毒性二茂铁衍生物 1、2 和 5 遵循基于二茂铁的氧化还原行为，但衍生物 3、4、6 和 7 表现出更复杂的机制。这些复杂的机制与更有效的细胞毒活性一致。穆斯堡尔光谱参数反映了非常小的取代基影响。
• Heteronuclear complexes containing the N,N′-di(2-pyridyl)amidocarboxylferrocene ligand
  作者：Mathieu Auzias、Bruno Therrien、Georg Süss-Fink

  DOI：10.1016/j.ica.2012.01.016

  日期：2012.5

  The ferrocene-derived ligand (NC5H4)(2)NOC-C5H4FeC5H5 reacts with arene ruthenium complexes [(eta(6)-arene)RuCl2](2) to give the cationic complexes [(eta(6)-p-(PrC6H4Me)-Pr-i)RuCl(NC5H4)(2)NOC-C5H4FeC5H5}](+) (1) and [(eta(6)-C6Me6)RuCl(NC5H4)(2)NOC-C5H4FeC5H5}](+) (2), isolated as the hexafluorophosphate and tetrafluoroborate salts, respectively, while the reaction with K2PtCl4 yields the neutral complex PtCl2(NC5H4)(2)NOC-C5H4FeC5H5} (3). The molecular structures of 2 and 3 were confirmed by single-crystal X-ray diffraction. (C) 2012 Elsevier B.V. All rights reserved.
• Synthesis and properties of new Mo(II) complexes with N-heterocyclic and ferrocenyl ligands
  作者：Susana Quintal、Serena Fedi、Jacopo Barbetti、Patrícia Pinto、Vitor Félix、Michael G.B. Drew、Piero Zanello、Maria José Calhorda

  DOI：10.1016/j.jorganchem.2010.11.024

  日期：2011.5

  New Mo(II) complexes with 2,2'-dipyridylamine (L1), [Mo(CH3CN)(eta(3)-C3H5)(CO)(2)(L1)]OTf (C1a) and [MoBr(eta(3)-C3H5)(CO)(2)(L1)}(2)(4,4'-bipy)](PF6)(2) (C1b), with [bis(2-pyridyl)amino]carbonyl}ferrocene (L2), [MoBr(eta(3)-C3H5)(CO)(2)(L2)] (C2), and with the new ligand N,N-bis(ferrocenecarbonyl)-2-aminopyridine (L3), [MoBr(eta(3)-C3H5)(CO)(2)(L3)] (C3), were prepared and characterized by FTIR and H-1 and C-13 NMR spectroscopy. C1a, C1b, L3, and C2 were also structurally characterized by single crystal X-ray diffraction. The Mo(II) coordination sphere in all complexes features the facial arrangement of allyl and carbonyl ligands, with the axial isomer present in C1a and C2, and the equatorial in the binuclear C1b. In both C1a and C1b complexes, the L1 ligand is bonded to Mo(II) through the nitrogen atoms and the NH group is involved in hydrogen bonds. The X-ray single crystal structure of C2 shows that L2 is coordinated in a kappa(2)-N,N-bidentate chelating fashion. Complex C3 was characterized as [MoBr(eta(3)-C3H5)(CO)(2)(L3)] with L3 acting as a kappa(2)-N,O-bidentate ligand, based on the spectroscopic data, complemented by DFT calculations.The electrochemical behavior of the monoferrocenyl and diferrocenyl ligands L2 and L3 has been studied together with that of their Mo(II) complexes C2 and C3. As much as possible, the nature of the different redox changes has been confirmed by spectrophotometric measurements. The nature of the frontier orbitals, namely the localization of the HOMO in Mo for both in C2 and C3, was determined by DFT studies. (C) 2010 Elsevier B.V. All rights reserved.