1-ferrocenoyl-1H-imidazole | 403819-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-ferrocenoyl-1H-imidazole
• 英文别名: ferrocenoyl imidazole；ferrocenoyl imidazolide；ferrocenyl imidazole；(η5-C5H5)Fe(η5-C5H4CON2C3H3)；[(η5-C5H5)Fe(η5-C5H4)CO(imidazole)]；FcCO(imidazole)；cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(imidazol-1-yl)methanone;iron(2+)
• CAS: 403819-33-0
• 化学式: C₁₄H₁₂FeN₂O
• 分子量: 280.109
• InChiKey: DBILBNCZDPNOSR-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：

  1-ferrocenoyl-1H-imidazole 、 lithium aluminium tetrahydride 以 乙醚 为溶剂， 以89%的产率得到二茂铁甲醇
  参考文献：
  名称：

  对二茂铁酰基衍生物化学的研究。二茂铁酰基咪唑啉及其衍生物的合成与反应

  摘要：

  二茂铁酰基咪唑啉化物易于从二茂铁羧酸一步合成。它是一种红色结晶化合物，在黑暗中于<5°C时稳定，可作为有效的二茂铁酰基等同物。它与醇盐快速反应生成酯，与硫醇盐迅速生成硫酯。它与Lawesson试剂的反应产生了二亚铁二茂铁酰基二硫化物。通过使二茂铁酰基咪唑啉化物与过氧化氢反应来制备二茂铁酰基过氧化氢的尝试是失败的。二茂铁酰基咪唑啉化物通过与二茂铁基-锂反应，一步转化为三茂铁基甲醇和二茂铁基酮。描述了二茂铁基苯基硫化物和二茂铁基二硫化物的X射线晶体结构。

  DOI：

  10.1016/s0022-328x(01)00915-9
• 作为产物：
  描述：

  咪唑 、 ferrocenoyl hydroxybenzotriazole ester 在 Et₃N 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到1-ferrocenoyl-1H-imidazole
  参考文献：
  名称：

  Ferrocene-histidine conjugates: N-ferrocenoyl-histidyl(imN-ferrocenoyl)methylester: synthesis and structure

  摘要：

  The preparation of the new ferrocenoyl histidyl conjugates N-Fc-His-OMe (2) and N-Fc-His(epsilon-N-Fc)-OMe (3) and of a simple ferrocenoyl imidazole conjugate Fc-Im (4) is reported together with their spectroscopic and electrochemical characterization. The electrochemistry of 3 exhibits two fully reversible one-electron. oxidations, which are due to the stepwise oxidation of the two ferrocenoyl groups. The crystal structure of 3 shows the difference in the chemical environment of the two Fc groups, one being attached to the alpha-N and one being attached to the epsilon-N of the imidazole of histidine. There is no discernible intermolecular interaction present in the crystal structure. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00182-7

文献信息

• Synthesis and characterization of palladium(II) and platinum(II) complexes with ferrocenylimidazole
  作者：Vincent O. Nyamori、Douglas Onyancha、Cedric W. McCleland、Christopher Imrie、Thomas I.A. Gerber

  DOI：10.1016/j.jorganchem.2008.12.041

  日期：2009.4

  The synthesis and characterization of ferrocenylimidazole complexes of platinum(II) and palladium(II) are described. Reaction of ferrocenylimidazoles with K2MCl4 (M = Pd, Pt) using a biphasic system of dichloromethane and ethanol/water provided the corresponding complexes 2a–2j in good yields. New synthetic routes for the synthesis of ferrocenylbenzylethers 2k–2o, bis(4-ferrocenylbenzyl)carbonate [2p]

  描述了铂（II）和钯（II）的二茂铁基咪唑配合物的合成和表征。使用二氯甲烷和乙醇/水的双相系统，二茂铁基咪唑与K 2 MCl 4（M = Pd，Pt）的反应以高收率提供了相应的配合物2a-2j。还描述了合成二茂铁基苄基醚2k-2o，双（4-二茂铁基苄基）碳酸酯[ 2p ]和4-二茂铁基苄基乙酸酯[ 2q ]的新合成路线。这些产物通过使4-二茂铁基苄基-1 H-咪唑-羧酸盐与K 2 PtCl 4在各种条件下反应而获得。化合物也可以通过不使用铂盐的替代途径获得2k–2o。报道了2b，2q的晶体结构和形成2k，2p和2q的合理机理。
• 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。
• CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine–Chalcone Hybrids
  作者：António Dembo、Etelka Ferenczi、Tamás Jernei、Andrea Bor、Zsuzsanna Schelz、István Zupkó、Szilárd Varga、Antal Csámpai

  DOI：10.3390/molecules29020375

  日期：——

  aldehyde-forming hydrolytic fission of the enone C=C bond in a substituent-, solvent- and copper load-dependent manner. The experienced hydrolytic stability of the hybrids obtained by cycloadditions with ortho-azidochalcones was interpreted in terms of relative energetics, DFT reactivity indices and MO analysis of simplified models of two isomer copper–enone complexes. The novel hybrids were evaluated on HeLa

  通过三种 CuAAC 化学方法制备了一系列新型三唑-拴系二碳烯酰氨基取代的金鸡纳-查尔酮杂化物以及两种具有代表性的苯甲酰氨基取代的参比化合物。根据低催化剂负载量尝试转化的有限成功或完全失败，通过 DFT 建模研究，我们证明大部分 Cu（I） 离子可以被螯合，从而被困在鸟月氨基酸取代的金鸡纳片段和查尔酮残基的所有可接近的配位位点中。因此，使用更多的催化剂来获得可接受的收率;然而，与对叠氮螺的环加成反应伴随着烯酮 C=C 键的部分或完全形成醛的水解裂变，以取代基、溶剂和铜负载依赖性方式。通过邻叠极锥进行环加成反应获得的杂化物的经验水解稳定性，根据两种异构体铜-烯酮配合物的简化模型的相对能量学、DFT 反应性指数和 MO 分析进行解释。在 HeLa、MDA-MB-231 和 A2780 细胞系上评估了新型杂交体，并在低至亚微摩尔浓度下显示出显著活性。在烯酮部分携带 3,4,5-三甲氧基苯基残基的
• 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.