{[4-(methoxycarbonyl)phenyl]ethynyl}ferrocene | 173987-77-4

• 英文名称: {[4-(methoxycarbonyl)phenyl]ethynyl}ferrocene
• 英文别名: 1-(4-(methoxycarbonyl)phenyl)-2-ferrocenylacetylene；methyl 4-[(ferrocenyl)ethynyl] benzoate
• CAS: 173987-77-4
• 化学式: C₂₀H₁₆FeO₂
• 分子量: 344.193
• InChiKey: VMJNXDHCJKJKOM-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：

  N-(1,3-二甲基丁基)-N'-(甲基苯基)苯-1,4-二胺 、 {[4-(methoxycarbonyl)phenyl]ethynyl}ferrocene 以 甲苯 为溶剂， 反应 16.0h， 以61%的产率得到1-ferrocenyl-2-[4-(methoxycarbonyl)phenyl]-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Synthesis, Molecular Structure, and Electrochemistry of 1‐Ferrocenyl‐1,2‐dicarba‐ closo ‐dodecaboranes

  摘要：

  AbstractBis(dimethylsulfido)decaborane, 6,9‐(Me2S)2‐arachno‐B10H12, reacts smoothly with ferrocenyl alkynes FcC≡CR [1a–h; Fc = ferrocenyl, R = H (1a), CH3 (1b), Ph (1c), 4‐MeO2CC6H4 (1d), Fc (1e), C≡CFc (1f), C(O)CH3 (1g), and CO2CH2CH3 (1h)] to afford the corresponding 1‐ferrocenyl‐1,2‐dicarba‐closo‐dodecaboranes 2a–h in good yields. Ester 2h was further reduced to the respective hydroxymethyl derivative, 1‐Fc‐2‐CH2OH‐1,2‐closo‐C2B10H10 (3). The reaction of 6,9‐(Me2S)2‐B10H12 with FcC≡CSiMe3 proceeded in a different manner to produce (among other products) an SMe2 adduct of an opened decaborane substituted with a 2‐ferrocenyl‐2‐(trimethylsilyl)ethen‐1‐yl group (4). This compound probably results through hydroboration of the starting alkyne and migration of the SiMe3 group. All prepared compounds were characterized by spectroscopic methods (1H, 13C, and 11B NMR spectroscopy, IR spectroscopy, and mass spectrometry), and their molecular structures were determined by single‐crystal X‐ray diffraction analysis. In addition, the compounds were studied by cyclic and differential pulse voltammetry on a platinum disc electrode to reveal simple ferrocenyl‐centered oxidations for the singly ferrocenylated carboranes and two consecutive oxidation waves for compounds 2e and 2f, which possess two ferrocenyl substituents.

  DOI：

  10.1002/ejic.201300110
• 作为产物：
  描述：

  1-ethynylferrocene 、 methyl 4-(prop-1-yn-1-yl)benzoate 在 Mo(CO)6 、 Cl₃C₆H₂OH 作用下， 以 甲苯 为溶剂， 以60%的产率得到{[4-(methoxycarbonyl)phenyl]ethynyl}ferrocene
  参考文献：
  名称：

  Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene

  摘要：

  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)

  DOI：

  10.1002/ejic.200800128

文献信息

• A Study of Polarization and Directing Effects of Unsymmetrical Alkynes Using Regioselective Pd-Catalyzed Bromoallylation
  作者：Nikola Topolovčan、Shuto Hara、Ivana Císařová、Zdeněk Tošner、Martin Kotora

  DOI：10.1002/ejoc.201901476

  日期：2020.1.16

  Pd‐catalyzed bromoallylation of unsymmetrical alkynes represents a simple approach towards functionalized olefins. The regioselectivity of this process is influenced by the direction of the polarization of the triple bond as well as by directing effects of a coordinating group in the pendant chain.

  Pd催化的不对称炔烃的溴代烯丙基化代表了一种简单的方法来官能化烯烃。该过程的区域选择性受三键极化方向以及侧链中配位基团的导向作用的影响。