2-amino-3-(pyridin-2-ylmethyleneamino)naphthalene-1,4-dione | 540729-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(pyridin-2-ylmethyleneamino)naphthalene-1,4-dione
• 英文别名: 2-Amino-3-(pyridin-2-ylmethylideneamino)naphthalene-1,4-dione
• CAS: 540729-34-8
• 化学式: C₁₆H₁₁N₃O₂
• 分子量: 277.282
• InChiKey: YSSNMTSNCFGDED-UHFFFAOYSA-N

物化性质

• 沸点：
  454.4±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-3-(pyridin-2-ylmethyleneamino)naphthalene-1,4-dione 、 zinc(II) chloride 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91.5%的产率得到
  参考文献：
  名称：

  Geometric and electrochemical properties of complexes consisting of two aminonaphthoquinone-bound Schiff-base ligands and MnII, FeII, NiII, CuII, or ZnII

  摘要：

  Novel compounds of metals (M = Mn-II, Fe-II, Cu-II, Zn-II) with aminonaphthoquinone-bound Schiff-base ligands (PyNq) were prepared with the form M(PyNq)(2). The resulting isostructural complexes formed NNN-type octahedral coordination geometry in crystals. The degree of distortion from the ideal octahedral structure depended on the ionic radius of the metal ion, with larger ions leading to greater distortion. Electrochemical studies showed that Fe-II(PyNq)(2) exhibited the greatest inter-ligand interaction of the tested compounds, resulting in a possible mixed-valence state in [Fe-II(PyNq)(2)](-). OFT calculations suggested that the efficient participation of Fell 3d orbitals in the LUMO would facilitate the inter-ligand interaction. The central metal ion was shown to be important to both the molecular and the electronic structures of the M(PyNq)(2) complexes, controlling their electron-responsive properties (redox functionalities). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.06.015
• 作为产物：
  描述：

  吡啶-2-甲醛 、 以 乙醇 为溶剂， 反应 1.0h， 以1.34 g的产率得到2-amino-3-(pyridin-2-ylmethyleneamino)naphthalene-1,4-dione
  参考文献：
  名称：

  Intermolecular charge transfer facilitated synthesis and spectral characterization of Schiff bases of a weak nucleophile 2,3-diamino-1,4-naphthoquinone

  摘要：

  通过添加六甲基苯 (HMB)，开发了一种在弱亲核试剂 2,3-二氨基-1,4-萘醌和醛之间形成新型席夫碱的新合成方案。该反应的驱动力是 HMB 和 DANQ 之间的分子间 CT 相互作用，导致亲核性增强，光谱和从头算计算证明了这一点。化合物的结构经UV-vis、IR、1H NMR、13C NMR和元素分析确证。该方法的优点是反应条件温和、产物收率高、操作简单、后处理容易。

  DOI：

  10.1039/c2ra21372a

文献信息

• Synthesis of Novel Lanthanide Complexes with Quinone-containing Ligands and Their Redox Controlled Magnetic Interaction
  作者：Takuya Nankawa、Masayuki Watanabe、Masaki Murata、Hiroshi Nishihara

  DOI：10.1246/cl.2003.286

  日期：2003.3

  New lanthanide-quinone and semiquinone complexes with the formula [Ln(L)2(OTf)3] and [Ln(L′)2(OTf)] (Ln = La, Gd, and Yb; OTf = CF3SO3−; L = aminoquinone ligand; L′ = aminosemiquinone ligand), respectively, were synthesized, and the magnetic interaction between f-electrons and organic radicals was revealed.

  分别合成了[Ln(L)2(OTf)3]和[Ln(L′)2(OTf)]（Ln = La、Gd 和 Yb；OTf = CF3SO3-；L = 氨基醌配体；L′ = 氨基半醌配体）的新型镧系醌和半醌配合物，并揭示了 f 电子与有机自由基之间的磁相互作用。