[2-(4-cyanophenyl)ethynyl]ferrocene | 120015-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(4-cyanophenyl)ethynyl]ferrocene
• 英文别名: [(4-cyanophenyl)ethynyl]ferrocene；[(ferrocenyl)CC(C6H4-4-CN)]；cyclopenta-1,3-diene;4-(2-cyclopenta-2,4-dien-1-ylethynyl)benzonitrile;iron(2+)
• CAS: 120015-71-6
• 化学式: C₁₉H₁₃FeN
• 分子量: 311.166
• InChiKey: PIESLCBEQMCZQE-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：

  bis(trifluoromethanesulphonato)bis(triphenylphosphine)palladium(II) 、 [2-(4-cyanophenyl)ethynyl]ferrocene 以 二氯甲烷 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  4-Ethinyl-benzonitrile-ferrocenes bridged by a Pd(PPh3)2 unit; the solid-state structure of (η5-C5H5)Fe(η5-C5H4CCC6H4CN-1,4)

  摘要：

  The trinuclear Fc-Pd-Fc complex [(FcC drop CC6H4C dropN-1,4)(2)Pd(PPh3)(2)] (OTf)(2) (5) [Fc = (eta (5)-C5H5)Fe(eta (5)-C5H4)] is accessible by the reaction of FcC drop CC6H4C dropN-1,4 (3) with (Ph3P)(2)Pd(OTf)(2) (4) in a 2:1 molar ratio. In 5 the corresponding late transition metal centers are linked by C5H4C drop CC6H4C dropN-1,4 pi -conjugated organic units. The result of the X-ray structure analysis of 3, which itself can be synthesised by a Sonogashira coupling of FcC drop CH (1) with BrC6H4C dropN-1,4 (2), is reported. Complex 3 crystallises in the monoclinic space group P2(1) with the following cell parameters: a = 9.6598(6), b = 7.3185(5), c = 10. 1910(7) Angstrom, beta = 98.876(3)degrees, V= 711.80(8) A(3) and Z = 2. In 3 the cyclopentadienyl ligands are rotated by 4.1(2)degrees and therefore possess an almost eclipsed conformation. With respect to the eta (5)-coordinated C5H4 group, the C6H4 unit is tilted by 69.87(13)degrees. Electrochemical studies on 3 show that the Fe(II)/Fe(III) oxidation process appears to be reversible and is shifted to a more positive value when compared to the FcH/FcH(+) couple. An even more positive value is observed for 5. A reason for this behaviour is presented. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00904-4
• 作为产物：
  描述：

  二茂铁乙炔 、 4-溴苯腈 以 not given 为溶剂， 生成 [2-(4-cyanophenyl)ethynyl]ferrocene
  参考文献：
  名称：

  有机金属π-镊子，NCN钳子和二茂铁在多金属过渡金属配合物的合成中作为分子“ Tinkertoys”

  摘要：

  这篇综述通过分子“ Tinkertoy”方法描述了早晚异二，异三和异四金属过渡金属配合物的合成，反应化学，结构和键合。作为不同金属原子之间的连接单元，可以使用π共轭的富含碳的有机和/或无机基团。还分别给出了这种一维分子线分子，配位聚合物，星形结构和树状取向过渡金属物种的电化学行为。

  DOI：

  10.1021/om058042p

文献信息

• Ferrocenes Bearing Highly Extended π Systems with Nitrile, Nitro, and Dimethylamino End Groups
  作者：Nico Krauße、Holger Butenschön

  DOI：10.1002/ejoc.201402831

  日期：2014.10

  precedence, may serve as points of attachment to gold surfaces. A crystal structure analysis of an unusual diferrocenylethyne derivative is included. In addition, one representative with a push-pull disubstitution that has a nitro and a dimethylamino end group is presented. Many of the prepared compounds have been characterized by cyclic voltammetry.

  低聚亚苯基-乙炔是用于分子电子学的一类流行的分子线。用 1,1'-二茂铁部分替代部分而非全部 1,4-亚苯基单元会产生刚性较低的实体，且构象灵活性有限。在这个概念内，提出了一些带有芳基乙炔基或 4-（芳基乙炔基）苯基取代基的 1,1'-二取代二茂铁的合成。与之前制备的具有硫端基的相关化合物相比，这里介绍的版本具有腈端基，根据报道的优先顺序，它可以作为金表面的连接点。包括对一种不寻常的二二茂铁基乙炔衍生物的晶体结构分析。此外，还介绍了具有硝基和二甲氨基端基的推拉双取代的代表。
• Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene
  作者：Tomáš Bobula、Jason Hudlický、Petr Novák、Róbert Gyepes、Ivana Císařová、Petr Štěpnička、Martin Kotora

  DOI：10.1002/ejic.200800128

  日期：2008.9

  AbstractCatalysts formed in situ from [Mo(CO)6] and halophenols in dichloromethane efficiently promote cross metathesis reactions of (prop‐1‐yn‐1‐yl)ferrocene with various functionalized alkynes to give the corresponding alkynylferrocenes with good selectivity and yields. Optimization of the reaction conditions by changing the phenol component has been carried out, revealing a critical influence of the phenol structure on the reaction yield. The structures of selected compounds were determined by single‐crystal X‐ray diffraction, and the results (particularly the crystal packing) were correlated with DFT calculations. In addition, the series of alkynes 4‐XC6H4C≡CFc (Fc = ferrocenyl) differing by the substituent X was studied by electrochemical methods, manifesting a good correlation between the redox potential of the ferrocene/ferrocenium couple and the Hammett σp constants of the remote substituents X. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)