N-(2-pyridylmethyl)ferrocene-1-carboxamide | 220113-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(2-pyridylmethyl)ferrocene-1-carboxamide
• 英文别名: ((2-pyridylmethylamino)carbonyl)ferrocene；cyclopenta-1,3-diene;iron(2+);N-(pyridin-2-ylmethyl)cyclopenta-1,3-diene-1-carboxamide
• CAS: 220113-14-4
• 化学式: C₁₇H₁₆FeN₂O
• 分子量: 320.174
• InChiKey: IIHKDNMZCLAANN-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 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：

  碘苯 、 N-(2-pyridylmethyl)ferrocene-1-carboxamide 在 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 以54%的产率得到2,5-bisphenyl-N-(2-pyridylmethyl)ferrocene-1-carboxamide
  参考文献：
  名称：

  钯催化Ç ？通过使用8-氨基喹啉作为可移动的导向基团对二茂铁羧酸进行H官能化

  摘要：

  已开发出一种温和有效的钯催化合成方法来使N-（喹啉-8-基）二茂铁羧酰胺的CH功能化。含有I，NO 2，CN，COMe，CO 2 Et和NH官能团的各种芳基碘化物以及烷基碘化物与P茂铁羧酰胺成功地进行了Pd催化的分子间碳-碳键形成反应，从而导致了各种各样的双（芳基/烷基）二茂铁甲酰胺，收率为34–92％。二茂铁的C交叉耦合利用芳族碘化物的H键也可以利用经济的Ni催化剂来实现。此外，在钯催化的反应条件下，以碳酸氢钠为碱，以二苄基磷酸为添加剂，研究了二茂铁甲酰胺的选择性单烷基化。随后，从双（芳基）二茂铁羧酰胺中除去导向基团8-氨基喹啉，生成带有通用甲基酯和甲醛官能团的双（芳基）二茂铁。

  DOI：

  10.1002/adsc.201500791
• 作为产物：
  描述：

  2-氨甲基吡啶 、 1-(ferrocenylcarbonyl)-1H-benzotriazole 以 氯仿 为溶剂， 以93%的产率得到N-(2-pyridylmethyl)ferrocene-1-carboxamide
  参考文献：
  名称：

  Microwave assisted synthesis of ferrocene amides

  摘要：

  A new microwave assisted synthesis methodology has been presented for the preparation of the ferrocene amides. Ferrocene carboxylic acid was derivatised using direct 1H-Benzotriazole/SOCl2 methodolgy to prepare N-ferrocenoyl benzotriazole as a new starting material for the functionalization of ferrocene ring. N-ferrocenoyl benzotriazole was reacted with mono- and di-amines under microwave irradiation to prepare ferrocene mono- and di-amides in high purity and in good yield. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2008.05.023

文献信息

• Cobalt‐Catalyzed C−H Alkoxylation of Ferrocenes with Alcohols under Mild Conditions
  作者：Zhuo‐Zhuo Zhang、Jie Cheng、Qi‐Jun Yao、Qiang Yue、Gang Zhou

  DOI：10.1002/adsc.202100423

  日期：2021.8.13

  protocol for synthesis of oxy-substituted ferrocenes via cobalt-catalyzed direct C−H alkoxylation under mild conditions. Notably, alcohol serves as an both alkoxide reagent and a solvent. Various ferrocene amides including estrone-derived ferrocene amide are compatible with these reaction conditions. Moreover, control experiments suggested that this alkoxylation might undergo a Co(III)/Co(IV)/Co(II) catalytic

  在本文中，我们报告了在温和条件下通过钴催化直接 CH 烷氧基化合成氧取代二茂铁的方案。值得注意的是，醇既是醇盐试剂又是溶剂。包括雌酮衍生的二茂铁酰胺在内的各种二茂铁酰胺与这些反应条件相容。此外，对照实验表明这种烷氧基化可能会经历 Co(III)/Co(IV)/Co(II) 催化循环。
• The effect of protonation on the spectroscopic and redox properties of a series of ferrocenoyl derivatives
  作者：Jonathan D. Carr、Simon J. Coles、William W. Hassan、Michael B. Hursthouse、K. M. Abdul Malik、James H. R. Tucker

  DOI：10.1039/a807453d

  日期：——

  ferrocenoyl derivatives, containing pyridine (1–4) and benzene (5) moieties, were synthesised and characterised. The effect on the spectroscopic and redox properties of these compounds upon addition of H+ was studied, with NMR studies indicating that protonation took place at the pyridine nitrogens of 1–4. A crystal structure determination of the bis(amide) derivative 4 revealed the presence of two intramolecular

  合成并表征了五种含吡啶（1-4）和苯（5）部分的二茂铁酰基衍生物。添加H +对这些化合物的光谱学和氧化还原特性的影响进行了NMR研究，表明质子化是在1-4个吡啶氮处发生的。双（酰胺）衍生物4的晶体结构测定表明存在两个分子内氢键。这些在溶液中保持完整，但在质子化时裂解。质子化导致二茂铁受体1、2和4在以二茂铁为中心的氧化还原电势中发生阳极移位，并在1-4的电子和NMR光谱中发生变化。质子化后，在最低能量自旋允许的d-d带中发生了红移，仅对于那些还表现出明显的氧化还原反应的化合物才观察到。
• Two copper complexes based on ligand bearing ferrocene unit: Synthesis and structural characterization
  作者：Zhehui Weng、Zilu Chen、Suni Qin、Fupei Liang

  DOI：10.1016/j.ica.2009.04.009

  日期：2009.8

  The reaction of [(2-Pyridylmethylamino)carbonyl]ferrocene with Cu(ClO4)(2) center dot 6H(2)O under conventional condition in the absence of base affords a monocopper compound, [Cu(Hpmaf)(2)(CH3OH)(2)](ClO4)(2)] 1, while that under solvothermal condition in the presence of triethylamine gives a dicopper compound, [Cu-2(pmaf)(2)](ClO4)(2), (Hpmaf = [(2-Pyridylmethylamino) carbonyl] ferrocene). Both compounds were characterised by elemental analysis, IR and X-ray diffraction analysis. Compound 2 was further characterised by UV-vis and electron paramagnetic resonance (EPR), and the results indicate that it is a fully delocalised mixed-valence dicopper compound. This is the first example of mixed-valence dicopper compound containing ferrocene group. Published by Elsevier B.V.