N-(hexyl)-2-aza[3]ferrocenophane | 244272-21-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(hexyl)-2-aza[3]ferrocenophane
• 英文别名: N,N-bis(cyclopenta-2,4-dien-1-ylmethyl)hexan-1-amine;iron(2+)
• CAS: 244272-21-7
• 化学式: C₁₈H₂₅FeN
• 分子量: 311.25
• InChiKey: QJCVQXKHNOMMHA-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：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  N-(hexyl)-2-aza[3]ferrocenophane 、 碘甲烷 以 乙腈 为溶剂， 以68%的产率得到bis(cyclopenta-2,4-dien-1-ylmethyl)-hexyl-methylazanium;iron(2+);iodide
  参考文献：
  名称：

  Preparation and characterization of various N-substituted-2-aza-[3]-ferrocenophanes and their chemical and electrochemical properties

  摘要：

  RuCl2(PPh3)(3) catalyzed condensation of 1,1'-ferrocenedimethanol with primary amines afforded N-alkyl- or N-aryl-2-aza-[3]-ferrocenophanes which were characterized by H-1 and C-13 NMR spectra. X-ray crystallography of N-(4-butylphenyl)-2-aza-[3]-ferrocenophane unequivocally revealed its mononuclear structure. The N-C (aryl) bond distance is shorter than the N-CH2 single bond due to extension of pi-conjugation of the aromatic ring to the nitrogen atom. N-Hexyl-2-aza-[3]-ferrocenophane reacts with methyl iodide to give the N-methylated product which was characterized by NMR spectroscopy and X-ray crystallography. N-Aryl-2-aza-[3]-ferrocenopbanes exhibited reversible redox between ferrocene and ferrocenium cations and an irreversible oxidation peak at a higher oxidation potential. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00369-2
• 作为产物：
  描述：

  1,1'-dihydroxymethylferrocene 、 正己胺 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 not given 为溶剂， 以40%的产率得到N-(hexyl)-2-aza[3]ferrocenophane
  参考文献：
  名称：

  N-取代的2-氮杂-[3]-二茂铁。RuCl 2（PPh 3）3催化的新合成缩合反应，结构和电化学行为

  摘要：

  在RuCl 2（PPh 3）3催化剂存在下，1,1'-二茂铁二甲醇与芳基胺和烷基胺的反应导致CH 2 OH和NH基团缩合，得到N-烷基-（或N-芳基-）2 -氮杂-[3]-二茂铁。N-（4-丁基苯基）-2-氮杂-[3]-二茂铁oph烷的1 H-和13 C-NMR光谱和晶体学显示了所提出的结构。研究了N-芳基和N-烷基-2-氮杂-[3]-二茂铁oph烷的电化学氧化。

  DOI：

  10.1016/s0022-328x(99)00114-x

文献信息

• Structure and properties of protonated N-alkyl-2-aza[3]ferrocenophanes
  作者：Yuji Suzaki、Masaki Horie、Tatsuaki Sakano、Kohtaro Osakada

  DOI：10.1016/j.jorganchem.2006.04.005

  日期：2006.7

  Protonation of N-alkyl-2-aza[3]ferrocenophanes by HCl and NH4PF6 affords hexafluorophosphate salts having a trialkylammonium group. Structures of the protonated and unprotonated N-(p-methylbezyl)-2-aza[3]ferrocenophanes were determined by X-ray crystallography. Variable temperature C-13H-1} NMR spectra of the N-protonated N-hexyl-2-aza[3]ferrocenophane revealed inversion of the nitrogen of the 2-aza[3]ferrocenophane on the NMR time scale probably via partial deprotonation of the nitrogen atom. Cyclic voltammograms of the N-protonated compounds exhibited reversible redox peaks at higher potentials than those of the corresponding neutral ferrocenophanes. (c) 2006 Elsevier B.V. All rights reserved.