N,N'-bis(2-hydroxybenzylidene)-p-phenylenediamine | 5344-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(2-hydroxybenzylidene)-p-phenylenediamine
• 英文别名: N,N'-bis(salicylidene)-p-phenylenediamine；N,N′-bis(salicylidine)-p-phenylenediamine；N,N’-bis(salicylidene)-1,4-diaminophenylene；N,N′-bis(salicylidene)-p-phenylenediamine；2,2'-((1,4-phenylenebis(azanylylidene))bis(methanylylidene))diphenol；N,N'-bis(2-hydroxybenzylidene)benzene-1,4-diamine；N,N'-bis(salicylidine)-p-phenylenediamine；N,N'-p-phenylenebis(salicylideneimine)；1,4-bis(salicylidene)phenylenediamine；PPDA-HB；2,2'-[1,4-phenylenebis(nitrilomethylidyne)]bis-phenol；disalicylidene-p-phenylenediamine；Disalicyliden-p-phenylendiamin；N.N'-Disalicylal-p-phenylendiamin；2-[[4-[(2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol
• CAS: 5344-68-3
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: CJTQTLHLELHKEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-hydroxybenzylidene)-p-phenylenediamine 在 sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-[[4-[(2-羟基苯基)甲氨基]苯胺基]甲基]苯酚
  参考文献：
  名称：

  Studies on structurally different benzoxazines based on diphenols and diamines: Kinetics of thermal degradation and TG-FTIR studies

  摘要：

  Structurally different bisbenzoxazines (QB, RB, pHBA-pd and mHBA-pd) are synthesized using quinol, resorcinol, p-phenylenediamine and m-phenylenediamine and are thermally cured. The thermal stability of the materials was studied using TGA. The plate like structure resulting from the interlinking of the ladders by intermolecular hydrogen bonding provides thermal stability to poly(pHBA-pd). The kinetics of thermal degradation is followed using Vyazovkin and Friedman methods. The diphenol based polybisbenzoxazines show higher apparent activation energy for thermal degradation (Ea-D) (PQB = 252-330 kJ/mol than the diamine based polybisbenzoxazines (poly(pHBA-pd) = 98-188 kJ/mol). Aromatic amines are found to be released in considerable quantities from the diamine based polybisbenzoxazines whereas phenolics are released from diphenol based polybisbenzoxazines. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.tca.2015.09.006
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 N,N'-bis(2-hydroxybenzylidene)-p-phenylenediamine
  参考文献：
  名称：

  Senier; Shepheard, Journal of the Chemical Society, 1909, vol. 95, p. 1954

  摘要：

  DOI：

文献信息

• Design of a structural framework with potential use to develop balanced multifunctional agents against Alzheimer's disease
  作者：Neng Jiang、Xiao-Bing Wang、Zhong-Rui Li、Su-Yi Li、Sai-Sai Xie、Ming Huang、Ling-Yi Kong

  DOI：10.1039/c4ra10692j

  日期：——

  A series of small molecules had been designed, synthesized, and evaluated as multifunctional ligands against Alzheimer's disease (AD).

  一系列小分子已被设计、合成并评估为多功能配体，用于对抗阿尔茨海默病（AD）。
• Study of the chemical structure and their nematicidal activity of N ₂ O ₂ tetradentate Schiff base metal complexes
  作者：S.M. Abd El‐Hamid、S.A. Sadeek、N.S. Abd El‐Lattif

  DOI：10.1002/aoc.5010

  日期：2019.8

  Coordination compounds of Cu (II), Y (III), Zr (IV) and La (III) with the tetradentate Schiff base (H2L) obtained through the condensation of p‐phenylenediamine with salicylaldehyde under reflux conditions. The complexes were characterized by elemental analysis, magnetic susceptibility, molar conductance and also, with various spectroscopic techniques such as 1H NMR, UV–Vis., IR and XRD techniques

  Cu（II），Y（III），Zr（IV）和La（III）与四齿Schiff碱（H 2 L）的配位化合物是通过对苯二胺与水杨醛在回流条件下缩合而获得的。通过元素分析，磁化率，摩尔电导以及各种光谱学技术（例如1H NMR，UV-Vis。，IR和XRD技术。通过摩尔电导值确定配合物的电解性质。在这四个络合物中，配体螯合物通过偶氮甲碱氮和酚基的氧原子以四齿的方式起作用。电子光谱数据与八面体的几何结构一致。氮气中的热降解分析用于研究水分子的数量和位置。金属配合物的化学式由微观分析数据证实。活化热力学参数，例如E *，ΔH *，ΔS *和ΔG *是使用Coats Redfern（CR）和Horowitz-Metzeger（HM）方法根据DTG曲线在n = 1或n≠1。杀线虫活性表明，与其配合物相比，配体具有更高的活性。另外，金属络合物显示出良好的中等杀线虫活性。
• Synthesis of benzo fused dioxadiazasilamacrocycles via remote dianion cyclization
  作者：Shweta Singh、Rajiv Kumar Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2012.09.106

  日期：2012.12

  An efficient and facile protocol for the synthesis of hitherto unreported benzo fused dioxadiazasilamacrocycles has been developed by intermolecular nucleophilic substitution of remote dianions generated in situ from symmetric and unsymmetric Schiff base ligands. The key step involves the initial formation of remote dianion from sequential deprotonation of phenolic OH groups of Schiff base ligands

  通过分子间亲核取代由对称和不对称席夫碱配体原位生成的远价二价阴离子，已开发出一种高效且简便的合成迄今未报道的苯并稠合的二恶二氮杂硅氮杂大环化合物的方案。关键步骤包括先从Schiff碱配体的酚OH依次脱质子化开始形成远端二价阴离子，然后攻击合适的二氯二有机硅烷，以高收率和高纯度得到所需化合物。
• α-AMINOPHOSPHONATES BEARING FREE HYDROXYL GROUPS IN THE AROMATIC RINGS. SYNTHESIS AND NMR CHARACTERIZATION
  作者：Salvatore Failla、Paolo Finocchiaro、Gerhard Hägele、Vitaly I. Kalchenko

  DOI：10.1080/10426509708031564

  日期：1997.9

  very good yields to mono- and bis-α-aminophosphonic acid dialkylesters containing the free phenolic hydroxyl group in a strategic position of the aromatic ring in order to enhance complexation with metal ions. This synthetic procedure is based on the addition of a solution of sodium dialkyl phosphite in phosphite to imine precursors. The addition reaction is highly stereospecific: only one diastereomer

  摘要 在本文中，我们描述了一种有用的合成方法，该方法可以产生非常好的单-和双-α-氨基膦酸二烷基酯，在芳环的战略位置含有游离酚羟基，以增强与金属离子的络合。该合成过程基于将亚磷酸二烷基酯钠溶液添加到亚胺前体中。加成反应是高度立体有择的：每个双-α-氨基膦酸二烷基酯仅形成一种非对映异构体。所有化合物均通过 NMR（1H 和 31P）和 FAB-MS 光谱表征。
• A neutral dinuclear Ir(<scp>iii</scp>) complex for anti-counterfeiting and data encryption
  作者：Yang Jiang、Guangfu Li、Weilong Che、Yingjie Liu、Bin Xu、Guogang Shan、Dongxia Zhu、Zhongmin Su、Martin R. Bryce

  DOI：10.1039/c7cc00769h

  日期：——

  A neutral dinuclear Ir(III) Schiff base complex PIBIP has been synthesized and shown to exhibit both piezochromic luminescence (PCL) and aggregation induced emission (AIE) behaviour.

  已合成了中性的双核Ir（III）Schiff碱复合物PIBIP，并显示出压电致变色发光（PCL）和聚集诱导发射（AIE）行为。