1-ferrocenoyl-1H-(2-aminobenzimidazole) | 913618-83-4

• 英文名称: 1-ferrocenoyl-1H-(2-aminobenzimidazole)
• 英文别名: ferrocenyl amidobenzimidazole；[(η5-C5H5)Fe(η5-C5H4)CO(2-aminobenzimidazole)]；FcCONH2benzim
• CAS: 913618-83-4
• 化学式: C₁₈H₁₅FeN₃O
• 分子量: 345.184
• InChiKey: BFQSUXGXNWLOHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 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：

  1-ferrocenoyl-1H-(2-aminobenzimidazole) 、 silver trifluoromethanesulfonate 以 二氯甲烷 为溶剂， 以91%的产率得到
  参考文献：
  名称：

  Synthesis and ligand properties towards gold and silver of the ferrocenylamidobenzimidazole ligand

  摘要：

  The treatment of FcCOCl (Fc = (C5H5)Fe(C5H4)) With amino benzimidazole in 1: 1 or 2:1 ratio gives the ferrocenyl-amido derivatives FcCO(benzimNH(2)) or (FcCO)(2)(NHbenzim), respectively. The reactivity of FcCO(benzimNH(2)) with silver or gold complexes has been studied. The reaction with the basic gold compounds [Au(acac)(PPh3)] or [O(AuPPh3)(3)]ClO4 occurs with deprotonation of the NH2 group and coordination of one or three gold(phosphine) fragments. The treatment of this ligand with silver compounds, such as Ag(OTf) or [Ag(OTf)(PPh3)], gives the complexes of stoichiometry [Ag(OTf)L] or [Ag(OTf)(PPh3)]. The ligand FcCO(benzimNH(2)) and the complex [Ag(OTf){FcCO(benzimNH(2))}(PPh3)] have been characterized by X-ray diffraction studies. DFT calculations were performed on models of this dimeric silver complex and showed that dimerization is energetically favourable, because Ag(I) achieves a four coordination environment, despite some bonds being relatively weak. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.06.025
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 ferrocenoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-ferrocenoyl-1H-(2-aminobenzimidazole)
  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

• New Polynuclear Mo–Fe Complexes with Ferrocenylamidobenzimidazole Ligands
  作者：Paulo N. Martinho、Susana Quintal、Paulo J. Costa、Serena Losi、Vitor Félix、M. Concepción Gimeno、Antonio Laguna、Michael G. B. Drew、Piero Zanello、Maria José Calhorda

  DOI：10.1002/ejic.200600296

  日期：2006.10

  The reaction between [Mo(eta(3)-C3H5)(CO)(2)(NCMe)(2)Br] (1) and the ferrocenylamidobenzimidazole ligands FcCO(NH(2)benzim) (L1) and (FcCO)(2)(NHbenzim) (L2) led to a binuclear (2) and a trinuclear (3) Mo-Fe complex, respectively. The single-crystal X-ray structure of [Mo(eta(3)-C3H5)(CO)(2)(L2)Br] [L2 = [(eta(5)-C5H5)Fe(eta(5)-C5H4CO)](2)(2-NH-benzimidazol-yl)}] shows that L2 is coordinated to the

  [MO(eta(3)-C3H5)(CO)(2)(NCMe)(2)Br] (1) 与二茂铁基氨基苯并咪唑配体 FcCO(NH(2)benzim) (L1) 和 (FcCO)( 2)(NHbenzim) (L2) 分别导致双核 (2) 和三核 (3) MO-Fe 复合物。[MO(eta(3)- )(CO)(2)(L2)Br] [L2 = [(eta(5)-C5H5)Fe(eta(5)- C5H4CO)](2)(2-NH-苯并咪唑基)}]表明L2与κ(2)-N中的内MO(eta(3)- )(CO)(2)基团配位， O-双齿螯合时尚，而 MO-II 中心显示伪八面体环境，Br 占据赤道位置。基于光谱数据、元素分析、电导率和 DFT 计算的组合，复合物 2 被公式化为 [MO(eta(3)- )(CO)(2)(L1)Br]。L1 充当 kappa(2)-N,N-二齿配体。在 L1
• 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.