N-ferrocenylcarboxybenzimidazole | 1021524-60-6

• 英文名称: N-ferrocenylcarboxybenzimidazole
• 英文别名: 1-ferrocenoyl-1H-benzimidazole；ferrocenyl benzimidazole；[(η5-C5H5)Fe(η5-C5H4)CO(benzimidazole)]；(η5-C5H5)Fe(η5-C5H4CON2C7H5)；FcCO(benzimidazole)
• CAS: 1021524-60-6
• 化学式: C₁₈H₁₄FeN₂O
• 分子量: 330.169
• InChiKey: SMSWPWAOBYLUPB-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：
  None
• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  N-ferrocenylcarboxybenzimidazole 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以44%的产率得到N-ferrocenylcarboxy-N-methylbenzimidazolium triflate
  参考文献：
  名称：

  带有环外N-酰基或N-磺酰基的（苯）咪唑-2-亚烷基的合成和反应性

  摘要：

  制备具有环外N-酰基或N-磺酰基的咪唑鎓盐和苯并咪唑鎓盐，并通过去质子化原位转化为相应的N-杂环卡宾。NHC被进一步转化为六族加合物（硫和硒）以及与Rh（I），Ir（I），Cu（I），Ni（II）和Fe（II）的金属配合物。所述Ñ酰基衍生物被发现是多向比水解降解更敏感Ñ磺酰基的化合物。对NHC-羰基配合物的红外光谱分析表明，与基于N-磺酰基的配体（TEP：2056-2061 cm ）相比，N-酰基NHCs的供体（TEP 2054-2055 cm -1）稍好。-1）。就其供体性质而言，这两种类型都可与环状单和二氨基甲酸酯类媲美。

  DOI：

  10.1016/j.jorganchem.2013.10.058
• 作为产物：
  描述：

  苯并咪唑 、 ferrocenoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-ferrocenylcarboxybenzimidazole
  参考文献：
  名称：

  二茂铁衍生物的电化学研究和潜在的抗癌活性

  摘要：

  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。

  DOI：

  10.1080/00958972.2016.1257125

文献信息

• Silver(I) and copper(I) complexes with ferrocenyl ligands bearing imidazole or pyridyl substituents
  作者：Susana Quintal、M. Concepción Gimeno、Antonio Laguna、Maria José Calhorda

  DOI：10.1016/j.jorganchem.2009.11.013

  日期：2010.2

  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.
• Synthesis and properties of new trinuclear Mo(II) complexes containing imidazole and benzimidazole ferrocene units
  作者：Susana Quintal、João Matos、Inês Fonseca、Vitor Félix、Michael G.B. Drew、Nuno Trindade、Margarida Meireles、Maria José Calhorda

  DOI：10.1016/j.ica.2007.05.039

  日期：2008.5

  The reaction of FcCOC1 (Fc = (C5H5) Fe(C5H4)) with benzimidazole or imidazole in 1: 1 ratio gives the ferrocenyl derivatives FcCO(benzim) (L1) or FcCO(im) (L2), respectively. Two molecules of L1 or L2 can replace two nitrile ligands in [Mo(eta(3)-C3H5)( CO)(2)(CH3CN)(2)Br] or [Mo(eta(3)-C5H5O)(CO)(2)(CH3CN)(2)Br] leading to the new trinuclear complexes [Mo(eta(3)-C3H5)(CO)(2)(L)(2)Br] (C1 for L = L1; C3 for L = L2) and [Mo(eta(3)-C5H5O)(CO)(2)(L)(2)Br] (C-2 for L = L1; C4 for L = L2) with L1 and L2 acting as N-monodentade ligands. L1, L2 and C2 were characterized by X-ray diffraction studies. [Mo(eta(3)-C5H5O)(CO) 2(L1)(2)Br] was shown to be a trinuclear species, with the two L1 molecules occupying one equatorial and one axial position in the coordination sphere of Mo(II). Cyclic voltammetric studies were performed for the two ligands L1 and L2, as well as for their molybdenum complexes, and kinetic and thermodynamic data for the corresponding redox processes obtained. In agreement with the nature of the frontier orbitals obtained from DFT calculations, L1 and L2 exhibit one oxidation process at the Fe(II) center, while C1, C3, and C4 display another oxidation wave at lower potentials, associated with the oxidation of Mo(II). (C) 2007 Elsevier B. V. All rights reserved.