1,1’-bis[1-(4-nitrophenylimino)ethyl]ferrocene | 182273-78-5

• 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: 1,1’-bis[1-(4-nitrophenylimino)ethyl]ferrocene
• 英文别名: [Fe((η5-C5H4)C(CH3)NC6H4-4-NO2)2]；1-cyclopenta-2,4-dien-1-yl-N-(4-nitrophenyl)ethanimine;iron(2+)
• CAS: 182273-78-5
• 化学式: C₂₆H₂₂FeN₄O₄
• 分子量: 510.332
• InChiKey: XERNADKYPCMYRI-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：

  1,1’-bis[1-(4-nitrophenylimino)ethyl]ferrocene 在 I₂ 作用下， 以 not given 为溶剂， 生成 [Fe((η5-C5H4)C(CH3)NC6H4-4-NO2)2](1+)
  参考文献：
  名称：

  From diacetylferrocene to 1,1′-ferrocenyldiimines: Substituent effects on synthesis, molecular structure, electrochemical behavior and optical absorption property

  摘要：

  A series of 1,1'-ferrocenyldiimines [Fe{(eta(5)-C5H4)-C(Me)N-R)(2)], where R = n-hexyl 1a, cyclohexyl 1b, phenyl 1c, 4-methoxyphenyl 1d, 3-methoxyphenyl 1e, 4-nitrophenyl 1f, and 3-nitrophenyl 1g, have been synthesized by reactions of ca. 1:2 M ratio of 1,1'-diacetylferrocene and the corresponding amines. While ca. 1:1 M ratio of the starting materials was employed, acetylferrocenylimines [Fe{(eta(5)-C5H4)-C(CH3)=O}{(eta(5)-C5H4)-C(CH3)=N-R}], where R = 4-nitrophenyl 2f, and 3-nitrophenyl 2g, were obtained. Single crystal X-ray structural analysis revealed that the two cyclopentadienyl rings in 1d, le, 1g, 2f, and 2g were antiperiplanar staggered, anticlinal eclipsed, anticlinal eclipsed/synclinal eclipsed, synclinal eclipsed, and synclinal eclipsed to each other in solid state, respectively. All synthesized ferrocene derivatives exhibited a reversible one-electron redox process in their cyclic voltammograms, and the values of their redox potentials relied on the R groups. The correlation between the redox potential and the Hammett substituent constant, sigma(p) was quite well, with a correlation coefficient of 0.98. The UV-vis spectra showed that their optical property was also substituent dependent. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.06.047
• 作为产物：
  描述：

  1,1'-diacetylferrocene 、 N-sulphinyl-p-nitroaniline 在 silica-supported Ti imido complex 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以43%的产率得到1,1’-bis[1-(4-nitrophenylimino)ethyl]ferrocene
  参考文献：
  名称：

  催化氧代/亚氨基异复分解法合成1,1'-二乙酰基二茂铁亚胺

  摘要：

  一种基于N-亚磺酰基胺和酮之间的羰基/亚氨基杂复分解的新颖C N键形成策略，由定义明确的二氧化硅支撑的Ti亚氨基配合物催化，用于制备一系列难以接近的1,1'-二乙酰基二茂铁酮亚胺。

  DOI：

  10.1016/j.jorganchem.2019.01.018

文献信息

• Synthesis and stereochemistry of bis(cyclopalladium) complexes of 1,1′-bis[1-(arylimino)ethyl]ferrocenes
  作者：Yang Tie Wu、Yuan Hong Liu、Yang Li、Zhu Qixiu

  DOI：10.1016/0277-5387(96)00101-5

  日期：1997.1

  Abstract Double cyclopalladation of 1,1′-bis[(arylimino)ethyl]ferrocenes with Li 2 PdCl 4 followed by treatment with PPh 3 afforded meso and dl stereoisomers of bis(palladium) complexes and the individual stereoisomers were isolated successfully by column chromatography. The composition and the structure of the metallocycles were characterized by elemental analysis, IR and 1 H NMR spectroscopy. A mechanism

  摘要用Li 2 PdCl 4对1,1'-双[（芳基）乙基]二茂铁进行双环钯反应，再用PPh 3处理得到双（钯）配合物的内消旋和dl立体异构体，并通过柱色谱法成功分离出各个立体异构体。通过元素分析，IR和1 H NMR光谱对金属环的组成和结构进行了表征。提出了在环钯反应中形成立体异构体的机理。