4-[(2-羟基亚苄基)氨基]苯酚 | 782-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-[(2-羟基亚苄基)氨基]苯酚
• 英文名称: 4-(salicylideneamino)phenol
• 英文别名: 2-(((4-hydroxyphenyl)imino)methyl)phenol；4-[(2-Hydroxybenzylidene)amino]phenol；2-[(4-hydroxyphenyl)iminomethyl]phenol
• CAS: 782-78-5
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: POLJRSQMPKDDIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-羟基亚苄基)氨基]苯酚 在 1,3,5-三溴-1,3,5-噻嗪烷-2,4,6-三酮 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以50%的产率得到水杨醛
  参考文献：
  名称：

  Selective conversion of C=N bonds to their corresponding carbonyl compounds by the tribromoisocyanuric acid/wet SiO2 system as a novel reagent

  摘要：

  Tribromoisocyanuric acid/wet SiO2 was used for the conversion of C=N bonds to their corresponding carbonyl compounds in oximes, semicarbazones, azines, and Schiff bases. The interesting feature of this system is that in those oximes, semicarbazones, azines, and Schiff bases which have conjugated or unconjugated C=C bonds, the C=N bond will selectively change to the relevant C=O bond while the conjugated or unconjugated C=C bond will remain intact.

  DOI：

  10.1007/s00706-011-0649-5
• 作为产物：
  描述：

  6-[1-(4-Hydroxy-cyclohexa-2,5-dienylideneamino)-meth-(E)-ylidene]-cyclohexa-2,4-dienone 以 甲醇 、 苯 为溶剂， 生成 4-[(2-羟基亚苄基)氨基]苯酚
  参考文献：
  名称：

  Csaszar, Jozsef, Acta Chimica Hungarica, 1990, vol. 127, # 2, p. 166 - 169

  摘要：

  DOI：

文献信息

• Study of the structure, prooxidative, and cytotoxic activity of some chelate copper(II) complexes
  作者：Vladimir P. Petrović、Marko N. Živanović、Dušica Simijonović、Jelena Đorović、Zorica D. Petrović、Snežana D. Marković

  DOI：10.1007/s11696-017-0200-1

  日期：2017.11

  The six chelate N,O-copper(II) complexes were synthesised starting from salicylaldehyde anil Schiff bases, as ligands. Their structure is elucidated using experimental and theoretical tools. In vitro biological activities, i.e. cytotoxic and prooxidative effects against human epithelial mammary gland/breast metastatic carcinoma MDA-MB-231, epithelial colorectal carcinoma HCT-116, and foetal lung fibroblast

  从水杨醛和席夫碱作为配体开始合成了六种螯合的N，O-铜（II）配合物。使用实验和理论工具阐明了它们的结构。还确定了所研究化合物对人上皮乳腺/乳腺癌转移癌MDA-MB-231，上皮结肠直肠癌HCT-116和胎儿肺成纤维细胞健康MRC-5细胞系的体外生物学活性，即细胞毒性和促氧化作用。配合物Cu-1，Cu-6尤其是Cu-7表现出明显的细胞毒性作用，IC 50值可与阳性对照CisPt的效果相比。此外，研究过的复合物在所有处理过的细胞系中均引起了极端的氧化和亚硝化应激。在HCT-116细胞和MRC-5细胞上观察到最显着的效果，而MDA-MB-231细胞对所研究的细胞系显示出更高的抗性，从而为我们提供了更具选择性的物质方向。
• UV-VIS, Fluorescence and Mass Spectrometry Investigation on the Transition Metal Ion Chelation of Two Bioisosteres of Resveratrol
  作者：Wen Qin、Biqun Zou、Ye Zhang、Xianghui Yi、Zhenghong Pan

  DOI：10.14233/ajchem.2013.13387

  日期：——

  2-[(o-Hydroxylphenylimino)methyl]phenol (OSAP) and 2-((p-hydroxylphenylimino)methyl)phenol (PSAP), two bioisosteres of the natural antioxidant resveratrol, are biologically interesting antioxidants. In order to probe whether they exert their antioxidant effect through metal ions chelation, the Cu(II) ion and Fe(II) ion chelating abilities of these compounds were measured by UV-VIS, fluorescence and mass spectroscopy, respectively. From UV-VIS spectra, the binding constants of OSAP with Cu2+ and Fe2+ were determined to be 7.58 × 103 and 2.22 × 103 M-1 by Benesi-Hildebrand method, while that of PSAP were found to be 6.20 × 103 and 2.08 × 104 M-1, respectively. From fluorescence quenching spectra, the Stern-Volmer quenching constants of OSAP with Cu2+ and Fe2+ were assessed to be 6.06 × 104 and 6.70 × 104 M-1, respectively, while that of PSAP were calculated to be 8.45 × 104 and 1.43 × 105 M-1. In addition, mass spectrometry studies showed that both OSAP and PSAP formed a 2:1 complex with ferrous when they were treated with Fe2+ in a 8:2 (v:v) methanol-water solution, respectively. The above results demonstrated the relatively significant role of the transition metal ion chelation in their antioxidant abilities.

  2-[(邻羟基苯亚氨基)甲基]苯酚(OSAP)和2-[(对羟基苯亚氨基)甲基]苯酚(PSAP)，作为天然抗氧化剂白藜芦醇的两个生物等排体，是生物学上有趣的抗氧化剂。为了探究它们是否通过金属离子螯合发挥抗氧化作用，分别使用紫外-可见光谱、荧光光谱和质谱法测量了这些化合物对Cu(II)离子和Fe(II)离子的螯合能力。从紫外-可见光谱中，通过Benesi-Hildebrand方法确定OSAP与Cu2+和Fe2+的结合常数分别为7.58 × 103和2.22 × 103 M-1，而PSAP的结合常数分别为6.20 × 103和2.08 × 104 M-1。从荧光淬灭光谱中，OSAP与Cu2+和Fe2+的Stern-Volmer淬灭常数分别评估为6.06 × 104和6.70 × 104 M-1，而PSAP的淬灭常数计算为8.45 × 104和1.43 × 105 M-1。此外，质谱学研究表明，当OSAP和PSAP分别在8:2（体积比）的甲醇-水溶液中处理时，它们均与Fe2+形成2:1的复合物。上述结果表明过渡金属离子螯合在其抗氧化能力中起着相对显著的作用。
• Dioxouranium(VI) thiocyanate complexes of schiff bases of p-nitro, chloro, bromo, hydroxy and methoxy aniline and salicylaldehyde
  作者：Wissam I. Azeez、Ali I. Abdulla

  DOI：10.1016/s0020-1693(00)81345-6

  日期：1985.7

  A series of dioxouranium(VI) complexes was synthesised with some Schiff base ligands containing substituent groups at para positions to CHN groups. These molecules were obtained by the condensation of para-nitro, chloro, bromo, hydroxy, methyl and methoxy aniline with salicylaldehyde. The bidentate ligands formed complexes of the type UO2(NCS)2 (X-N-Sal)n·mH2O, where n = 2, m = 3, x = NO2, Cl, Br

  合成了一系列二氧呋喃鎓（VI）配合物，其中一些席夫碱配体在CH=N基的对位含有取代基。这些分子是通过将对硝基，氯，溴，羟基，甲基和甲氧基苯胺与水杨醛缩合而获得的。双齿配体形成UO2（NCS）2（XN-Sal）n·mH2O型复合物，其中n = 2，m = 3，x = NO2，Cl，Br和OH； n = 2，m = 3，x = NO2。n = 3，m = 2，x = CH3和OCH3。电导率测量表明，所有配合物在硝基甲烷溶液中均为非电解质，而在DMF中，它们对应于1：1电解质。红外光谱数据表明，席夫碱的分子而不是阴离子与中心铀原子配位。红外和拉曼光谱表明，配合物UO2（NCS）2（XN-Sal）2·3H2O（X = NO2，Cl，Br）具有C2h分子对称性，而UO2（NCS）2（XN-Sal）3·2H2O（X = OCH3，CH3）具有C2v对称性。配合物中UO2（asym）（IR）和UO
• Facile synthesis, solublization studies and anti-inflammatory activity of amorphous zinc(II) centered aldimine complexes
  作者：Uzma ALI、Aneela MAALIK、Muhammad Babar TAJ、Ahmad RAHEEL、Ahmad Kaleem QURESHI、Muhammad IMRAN、Muhammad SHARIF、Syed Ahmad TIRMIZI、Sadia NOOR、Heba ALSHATER

  DOI：10.33224/rrch.2020.65.10.08

  日期：——

  In this study, Zn(II) centered complexes with aldimine derivatives were synthesized using green solvent, polyethylene glycol (PEG-400) and amorphous complexes were characterized by FT-IR, multinuclear (1H and 13C NMR), elemental and thermal analysis. Thermogravimetric analysis indicated the extended thermal stability of the synthesized complexes. All the Zn(II) complexes show very significant photoexcitation in the range of 318 – 384 nm and photoemission in the range of 502 – 562 nm. Among all the complexes, Zn(II) complex (3Zn) showed minimum band gap value, 2.35 eV. These amorphous complexes have been reported for their wide applications in biomedical sciences. The synthesized aldimine ligands and Zn(II) complexes were investigated for anti-inflammatory activity and these complexes showed more anti-inflammatory potential than the corresponding aldimine ligands. The solubilization of zinc complexes in sodium dodecyl sulphate was also investigated to reveal the interaction of metal complexes by using UV-Visible spectroscopy and electrical conductivity measurements.

  在这项研究中，使用绿色溶剂聚乙二醇（PEG-400）合成了以aldimine衍生物为中心的Zn(II)配合物，并通过FT-IR、多核（1H和13C NMR）、元素和热分析对非晶态配合物进行了表征。热重分析表明了合成配合物的延展热稳定性。所有的Zn(II)配合物在318-384 nm范围内表现出非常显著的光激发，502-562 nm范围内的光发射。在所有配合物中，Zn(II)配合物（3Zn）显示出最小的带隙值，为2.35 eV。这些非晶态配合物已被报道在生物医学科学中具有广泛的应用。合成的aldimine配体和Zn(II)配合物被用于抗炎活性的研究，这些配合物显示出比相应的aldimine配体更强的抗炎潜力。还研究了在十二烷基硫酸钠中的锌配合物的溶解度，通过紫外-可见光谱和电导率测量揭示了金属配合物的相互作用。
• Substituent effects on the absorption and vibrational spectra of some 2-hydroxy Schiff bases: DFT/TDDFT, natural bond orbital and experimental study
  作者：S. A. Elroby、S. Aboud、S. G. Aziz、R. Hilal

  DOI：10.1134/s0022476615030038

  日期：2015.6

  A set of 12 substituted SA derivatives is considered in the present work. The choice of these substituents aims to create a push-pull system on the SA basic structure which would shade light onto its photo physics. The electronic absorption spectra of SA are recorded in the UV-VIS region, in both polar and nonpolar solvents. Assignments of the observed electronic transitions are facilitated via time-dependent

  水杨基苯胺 (SA) 及其一些衍生物的电子结构通过实验和理论进行了研究。所研究化合物的平衡几何结构在 B3LYP/6-311++G** 理论水平确定。在目前的工作中考虑了一组 12 种取代的 SA 衍生物。这些取代基的选择旨在在 SA 基本结构上创建一个推拉系统，该系统将光线遮蔽到其光物理上。SA 的电子吸收光谱记录在 UV-VIS 区域，在极性和非极性溶剂中。通过在同一理论水平上的时间相关密度泛函理论 (TDDFT) 计算来促进观察到的电子跃迁的分配。确定了对每个激发态有贡献的电子配置，并表征了相关的 MO。根据自然键轨道 (NBO) 分析和供体和受体 MO 之间的二阶扰动相互作用来估计和讨论离域和分子内电荷转移的程度。根据基态和激发态极化率的差异讨论了溶剂对电子吸收光谱的影响。SA 及其衍生物的 FTIR 光谱是在 KBr 血小板中测量的。基于计算出的势能分布给出了详细的振动分配。识别表征