(6-chloroquinolin-2-yl)ferrocene | 1037364-61-6

• 英文名称: (6-chloroquinolin-2-yl)ferrocene
• 英文别名: 6-chloro-2-ferrocenylquinoline
• CAS: 1037364-61-6
• 化学式: C₁₉H₁₄ClFeN
• 分子量: 347.627
• InChiKey: JKAQWEFRJAGBPL-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

• 作为产物：
  描述：

  4-chloro-N-(ferrocenylmethylidene)aniline 、 乙醛 在 碘 作用下， 以 1,4-二氧六环 为溶剂， 以63%的产率得到(6-chloroquinolin-2-yl)ferrocene
  参考文献：
  名称：

  Synthesis of ferrocenyl quinolines

  摘要：

  A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.03.022

文献信息

• Efficient Synthesis of Ferrocenylquinolines via the Friedländer Reaction
  作者：Yuhua Long、Haifeng Zhang、Dingqiao Yang

  DOI：10.1080/00397911.2010.519090

  日期：2013.1.1

  Acylferrocenes 2a-c reacted with ortho-aminoarylaldehydes 1a-e via the Friedlander condensation reaction to afford the corresponding ferrocenylquinolines 3a-o in moderate yields in the presence of sodium ethoxide (30 mmol%) under mild reaction conditions. Under the same reaction conditions, 1,1'-diacetylferrocene 2d and 1,1'-dipropionylferrocene 2e reacted with ortho-aminoaldehydes 1a-e to afford the corresponding 1,1'-bis(substituted quinolin-2-yl) ferrocene derivatives 3p-t. The structures of compounds 3a-t were determined and characterized by infrared, H-1 NMR, mass spectrometry, and elemental analysis. The crystal structures of 3e and 3q were determined by x-ray crystallography.