4,4'-{[1,4-phenylenebis(azanylylidene)]bis(methanylidene)}bis[5-(hydroxymethyl)-2-methylpyridin-3-ol] | 156487-85-3

• 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: 4,4'-{[1,4-phenylenebis(azanylylidene)]bis(methanylidene)}bis[5-(hydroxymethyl)-2-methylpyridin-3-ol]
• 英文别名: N,N'-dipyridoxyl(1,2-diphenyldiamine)；4-[[2-[[3-Hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]phenyl]iminomethyl]-5-(hydroxymethyl)-2-methylpyridin-3-ol
• CAS: 156487-85-3
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: WUQFENYBXFMMOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  796.0±60.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4'-{[1,4-phenylenebis(azanylylidene)]bis(methanylidene)}bis[5-(hydroxymethyl)-2-methylpyridin-3-ol] 、 zinc diacetate 以 甲醇 为溶剂， 生成 (N,N′-phenylenebis(pyridoxyliminato))Zn
  参考文献：
  名称：

  Reactivity of monohydrogensulfide with a suite of pyridoxal-based complexes: A combined NMR, ESI-MS, UV–visible and fluorescence study

  摘要：

  In the present work, we explored the reactivity of HS- with a family of fluorescent metal complexes via a variety of spectroscopic techniques. The complexes under investigation are obtained by complexation of zinc or nickel with pyridoxal-based ligands. More specifically complexes 1 and 2 are zinc complexes namely L1 Zn(II) and L2Zn(II) where L1 stands for N,N'-phenylenebis(pyridoxyliminato) and L2 is N,N'-binaphthylenebis(pyridoxyliminato), whereas complex 3 is a nickel complex (L3Ni(II)) where L3 is N,N'-ethylenebis(pyridoxyliminato). A combination of NMR, ESI-MS, UV-vis and fluorescence experiments provide evidence that HS- binds the metal center in the case of complexes 1 and 3 whereas for complex 2, ZnS precipitation and hydrolysis of the organic ligand occur. Fluorescence experiments indicate that in the presence of HS- complex 1 undergoes a consistent fluorescence enhancement whereas for complex 3 the parent fluorescence exhibits a visible quenching. The results highlight the potential of complex 1 to be implemented as a HS- fluorescent sensor via a coordinative-based approach.

  DOI：

  10.1016/j.ica.2019.119235
• 作为产物：
  描述：

  吡哆醛 、 邻苯二胺 以 乙醇 为溶剂， 反应 7.0h， 以81%的产率得到4,4'-{[1,4-phenylenebis(azanylylidene)]bis(methanylidene)}bis[5-(hydroxymethyl)-2-methylpyridin-3-ol]
  参考文献：
  名称：

  吡ido醛与芳族二胺的反应

  摘要：

  通过吡ido醛与芳族二胺的反应获得吡rid醛单亚胺。试剂比例的改变或另一种芳族醛向反应中的引入导致对称和不对称的二亚胺的形成。在某些情况下，最初形成的二亚胺被转化为相应的苯并咪唑。吡ido醛与1，3-二氨基苯的反应产物具有呋喃吡啶结构。

  DOI：

  10.1007/s10593-020-02663-y

文献信息

• Synthesis, experimental and theoretical characterization of a Mn(II) complex of N,N′-dipyridoxyl(1,2-diaminobenzene)
  作者：Tina Toozandejani、S. Ali Beyramabadi、Hamed Chegini、Maryam Khashi、Ali Morsali、Mehdi Pordel

  DOI：10.1016/j.molstruc.2016.07.026

  日期：2017.1

  catalytic applications, synthesis of a Mn(II) complex of the N,N′-dipyridoxyl(1,2-diaminobenzene) [H 2L] Schiff-base has been reported. The Mn complex was characterized experimentally and theoretically. The optimized geometry and vibrational frequencies of the complex were computed by using the density functional theory (DFT) methods. In the optimized geometry of the octahedral complex, the dianionic L2−

  摘要 在此，跳到生物和催化应用，合成了 N,N'-二吡啶氧基（1,2-二氨基苯）[H 2L] 席夫碱的 Mn(II) 络合物。Mn 配合物在实验上和理论上进行了表征。使用密度泛函理论 (DFT) 方法计算了复合体的优化几何形状和振动频率。在八面体配合物的优化几何结构中，双阴离子 L2− 充当四齿配体。方形平面的四个配位位置已被 L2− 配体的两个偶氮甲碱氮和两个酚氧占据。两个配位的甲醇配体垂直于方形平面。此外，使用分子中的原子 (AIM) 分析研究了 Mn N 和 Mn O 键的性质。
• Cu(II) Complex of a Schiff Base Derived from Pyridoxal: Synthesis, Experimental Characterization, DFT Studies, and Aim Analysis
  作者：N. Samini、S. A. Beyramabadi、F. F. Bamoharram

  DOI：10.1134/s0022476619080067

  日期：2019.8

  A Cu(II) complex of the N,N′-dipyridoxyl(1,2-diaminobenzene) [=H2L] Schiff base is newly synthesized. The complex is characterized experimentally and theoretically. The density functional theory methods are employed to calculate the optimized geometry along with the natural bond orbital analysis and the vibrational frequency analysis of the complex. The computed IR frequencies are in agreement with

  新合成了 N,N'-二吡啶氧基（1,2-二氨基苯）[=H2L] 席夫碱的 Cu(II) 络合物。该复合物在实验和理论上进行了表征。使用密度泛函理论方法计算优化的几何形状以及配合物的自然键轨道分析和振动频率分析。计算出的 IR 频率与实验结果一致，证实了所提出的复合体几何结构的有效性。在八面体配合物的优化几何结构中，双阴离子 L2– 作为四齿配体。L2-配体的两个偶氮甲碱氮原子和两个酚盐氧原子占据配合物的四个正方形位置。此外，两个甲醇配体垂直于方形平面。前沿轨道之间的大能隙证明了复合物的稳定性。Cu-N 和 Cu-O 键的性质也通过分子中的原子分析进行研究。
• An aggregation-induced emissive pyridoxal derived tetradentate Schiff base for the fluorescence turn-off sensing of copper(<scp>ii</scp>) in an aqueous medium
  作者：Vinita Bhardwaj、Lavani Hindocha、SK Ashok Kumar、Suban K Sahoo

  DOI：10.1039/d1nj05523b

  日期：——

  In this study, a tetradentate Schiff base ligand L was synthesized by condensing o-phenylenediamine with two moles of pyridoxal. The solution of L in EtOH/DMSO showed aggregation-induced emission (AIE) behaviour with the addition of water. The weakly emissive L in EtOH/DMSO at 474/442 nm showed a blue-shifted fluorescence enhancement at 380 nm with the addition of water/HEPES buffer. The aggregation

  在这项研究中，通过将邻苯二胺与两摩尔吡哆醛缩合合成了四齿席夫碱配体L。L在 EtOH/DMSO 中的溶液在加入水时表现出聚集诱导发光 (AIE) 行为。加入水/HEPES 缓冲液后，EtOH/DMSO 中 474/442 nm 处的弱发射L在 380 nm 处显示出蓝移荧光增强。DLS 和 SEM 分析支持L的聚合。由于聚集时分子内旋转 (RIR) 的限制，C N 异构化的阻断将弱发射L转化为高蓝色荧光L。L的聚合体在混合 EtOH:HEPES 缓冲液（5% EtOH，pH = 7.4）介质中探索了金属离子的荧光传感。Cu 2+的加入与L以1:1 的结合比例形成复合物，由于Cu 2+的顺磁性和ESIPT 的抑制作用，L的荧光猝灭。通过紫外-可见和荧光技术估计的络合物L - Cu 2+的结合常数分别为1.36 × 10 4 M -1和3.63 × 10 4 M -1。L的猝灭荧光通过添加强螯合剂
• N,N′-dipyridoxyl Schiff bases: Synthesis, experimental and theoretical characterization
  作者：S. Ali Beyramabadi、Ali Morsali、Malihe Javan Khoshkholgh、Abbas Ali Esmaeili

  DOI：10.1016/j.saa.2011.08.067

  日期：2011.12

  Three N,N'-dipyridoxyl Schiff bases (L1, L2 and L3) have been newly synthesized and characterized by IR, (1)H NMR, mass spectrometry and elemental analysis. Their optimized geometries together with the theoretical assignment of the vibrational frequencies and the (1)H NMR chemical shifts of them have been computed by using density functional theory (DFT) method. In the optimized structures of the Schiff bases, two pyridine rings are not in a same plane; however the substitutions are essentially in the same plane with the pyridine rings. Also, the benzene ring(s) in the bridge region is (are) not in the same plane with the pyridine rings and azomethine moieties. In all the species, engagement in intramolecular-hydrogen bonds causes to weakness of the phenolic O-H bonds. Consistency between the theoretical results and experimental evidence confirms suitability of the optimized geometries for the synthesized Schiff bases. (C) 2011 Elsevier B.V. All rights reserved.