1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol | 20772-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol
• 英文别名: 2-[(4-methylphenylimino)methyl]-6-methoxyphenol；2-methoxy-6-[(4-methylphenyl)iminomethyl]phenol
• CAS: 20772-64-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: OYEREWRJWMPHMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trichlorotris(triphenylarsine)ruthenium(III) 、 1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol 在 Et₃N 作用下， 以 苯 为溶剂， 以70%的产率得到RuCl2(AsPh3)2(2-O-3-OMe-C6H3CHNC6H4Me-4)
  参考文献：
  名称：

  Ruthenium(III) Complexes Containing Monofunctional Bidentate Schiff Bases

  摘要：

  DOI：

  10.1080/00945710009351833
• 作为产物：
  描述：

  乙烷,三氯氟- 、 邻香草醛 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol
  参考文献：
  名称：

  席夫碱 2-[(4 甲基苯基亚氨基)甲基]-6-甲氧基苯酚的镍 (II) 配合物的合成、晶体结构和热分解动力学

  摘要：

  一种新的双核配合物[Ni2(H2O)L4]·5H2O，由螯合二齿和桥接三齿配位的2-[(4-甲基苯基亚氨基)甲基]-6-甲氧基苯酚(HL)席夫碱配体和水分子组成。一种传统方法。该配合物的结构通过 FTIR 和 UV/Vis 光谱和热重分析 (TG-DTG) 进行表征，并通过单晶 X 射线衍射进一步证实。其晶体结构为单斜晶系，空间群P21/c，a = 13.2837(5) Å, b = 27.3886(10) Å, c = 17.5415(6) Å, α = 90 º, β = 108.429(2) º , γ = 90 º, V = 6054.7(4) Å3, Z = 4。晶体结构显示存在Ni·Ni核，间距为3.183 Å。还研究了其热分解动力学。

  DOI：

  10.3390/molecules14072582

文献信息

• Synthesis, characterization and antimicrobial activity of copper(II) Schiff base adducts of some p-substituted aniline Schiff bases
  作者：A. O. Sobola、G. M. Watkins、R. O. Shaibu、S. Adewuyi、S. A. Amolegbe

  DOI：10.4314/bcse.v35i1.3

  日期：——

  The synthesis, characterization and antimicrobial activity of Cu(II) complexes of some p-substituted aniline Schiff base ligands have been carried out. The Schiff bases were obtained from salicylaldehyde and o-vanillin. The Cu(II) complexes have been characterized by elemental analysis, conductivity measurement, infrared and electronic spectral data. The complexes were obtained either as metal chelates [Cu(L)2] or Schiff base adducts (CuCl2.2LH).xH2O. The metal chelates were non-electrolytes while the Schiff base adducts exhibited 1:1 or 2:1 electrolytes in methanol. The Cu(II) complexes exhibited slight antimicrobial activity against Escherichia coli ATCC® 8739™*, Staphylococcus aureus subsp. aureus ATCC® 6538™*, Bacillus subtilis subsp. spizizenii ATCC® 6633™* and Candida albicans ATCC® 2091™*. The complexes exhibited significant antifungal activity.                     KEY WORDS: Metal Chelates, Schiff bases, Adducts, Cu(II) complexes, Salicylaldimines   Bull. Chem. Soc. Ethiop. 2021, 35(1), 33-42. DOI: https://dx.doi.org/10.4314/bcse.v35i1.3

  研究人员对一些对取代苯胺希夫碱配体的 Cu(II) 复合物进行了合成、表征和抗菌活性研究。这些希夫碱是从水杨醛和邻香兰素中获得的。Cu(II) 复合物通过元素分析、电导率测量、红外和电子光谱数据进行了表征。这些配合物以金属螯合物 [Cu(L)2] 或希夫碱加合物 (CuCl2.2LH).xH2O 的形式获得。金属螯合物是非电解质，而席夫碱加合物在甲醇中的电解质为 1:1 或 2:1。Cu(II) 复合物对大肠杆菌 ATCC® 8739™*、金黄色葡萄球菌亚种 ATCC® 6538™*、枯草杆菌亚种 spizenii ATCC® 6633™* 和白色念珠菌 ATCC® 2091™* 具有轻微的抗菌活性。这些复合物具有明显的抗真菌活性； ； 关键词：金属螯合物，席夫碱，加合物，Cu(II) 复合物，水杨醛亚胺 ； ； Bull.Chem.Soc.2021, 35(1), 33-42. ； DOI: https://dx.doi.org/10.4314/bcse.v35i1.3
• Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3-methoxybenzalideneanilines
  作者：Guan-Yeow Yeap、Sie-Tiong Ha、Nobuo Ishizawa、Katsumi Suda、Peng-Lim Boey、Wan Ahmad Kamil Mahmood

  DOI：10.1016/s0022-2860(03)00453-8

  日期：2003.9

  1-(4-chlorophenylimino)methyl}-2-hydroxy-3-methoxyphenol were adopted wherein the 4-chloro (4-Cl) and 4-methyl (4-CH3) containing compounds crystallized into orthorhombic lattice with a non-centrosymmetric space group P212121. The relationship between the stabilization of bonding involved in heteronuclear six-membered ring of the tautomer and the conformation of the molecules in crystal phase was reported.

  摘要 合成了 8 种衍生自 2-羟基-3-甲氧基苯甲醛和不同对位取代苯胺的席夫碱，并通过物理测量和 FT-IR 阐明了它们的结构。使用 1H、13C NMR 进行 NMR 分配，并辅以 2D COZY 同核、HMQC 和 HMBC 异核相关技术。发现模型化合物的 IR 光谱分析有助于理解这一系列烯醇-亚氨基互变异构体的稳定程度，它们在苯胺片段中具有不同的取代基。为了使固态互变异构体的稳定性合理化，采用1-(4-甲基苯基亚氨基)甲基}-和1-(4-氯苯基亚氨基)甲基}-2-羟基-3-甲氧基苯酚的晶体学数据，其中4-氯(4-Cl)和4-甲基(4-CH3) 的化合物结晶成正交晶格，具有非中心对称空间群 P212121。报道了互变异构体的异核六元环中键合的稳定性与分子在晶相中的构象之间的关系。
• Mechanically induced reactions in organic solids: liquid eutectics or solid-state processes?
  作者：Oleksandr Dolotko、Jerzy W. Wiench、Kevin W. Dennis、Vitalij K. Pecharsky、Viktor P. Balema

  DOI：10.1039/b9nj00588a

  日期：——

  The solvent-free reaction between o-vanillin and p-toluidine was investigated using NMR, DSC and XRD analyses. At room temperature, o-vanillin and p-toluidine react in a liquid eutectic formed upon grinding, while below 10 °C the same materials appear to react without the formation of a liquid phase, which most likely remains hidden behind solid reactants and reaction products.

  使用核磁共振、差示扫描量热法和X射线衍射分析研究了邻香草醛和对甲苯胺之间的无溶剂反应。在室温下，邻香草醛和对甲苯胺在研磨形成的液态共晶中发生反应，而在10°C以下，相同的材料似乎在没有形成液相的情况下发生反应，液相很可能隐藏在固态反应物和反应产物后面。
• Synthesis, Crystal Structure, and Kinetics of the Thermal Decomposition of the Nickel(II) Complex of the Schiff Base 2-[(4 Methylphenylimino)methyl]-6-methoxyphenol
  作者：Yan-Fang Wang、Jian-Feng Liu、Hui-Duo Xian、Guo-Liang Zhao

  DOI：10.3390/molecules14072582

  日期：——

  monoclinic system, space group P21/c with a = 13.2837(5) Å, b = 27.3886(10) Å, c = 17.5415(6) Å, α = 90 º, β = 108.429(2) º, γ = 90 º, V = 6054.7(4) Å3, Z = 4. The crystal structure reveals that there is a Ni·Ni core, with a separation of 3.183 Å. Its thermal decomposition kinetics were also studied.

  一种新的双核配合物[Ni2(H2O)L4]·5H2O，由螯合二齿和桥接三齿配位的2-[(4-甲基苯基亚氨基)甲基]-6-甲氧基苯酚(HL)席夫碱配体和水分子组成。一种传统方法。该配合物的结构通过 FTIR 和 UV/Vis 光谱和热重分析 (TG-DTG) 进行表征，并通过单晶 X 射线衍射进一步证实。其晶体结构为单斜晶系，空间群P21/c，a = 13.2837(5) Å, b = 27.3886(10) Å, c = 17.5415(6) Å, α = 90 º, β = 108.429(2) º , γ = 90 º, V = 6054.7(4) Å3, Z = 4。晶体结构显示存在Ni·Ni核，间距为3.183 Å。还研究了其热分解动力学。
• Synthesis, Crystal Structure and DNA-Binding of Lanthanum Complex with Schiff Base Derived from o-Vanillin and p-Toluidine
  作者：Xiao-Ju Chen、Wei-Ji Hu、Yi Qin、Guo-Liang Zhao

  DOI：10.14233/ajchem.2013.14388

  日期：——

  A new complex [La(NO3)3(C2H5OH)(C15H15NO2)2] was synthesized from lanthanum nitrate and Schiff base (C15H15NO2, derived form o-vanillin and p-toluidine) by refluxing in ethanol. Its crystal structure was determined by single crystal X-ray diffraction method. The complex is crystallize in triclinic, space group P-1, with a = 0.79851(3) nm, b = 1.47473(5) nm, c = 1.63872(6) nm, a = 73.546(2)º, b = 86.769(2)º, g = 79.767(2)º, V = 1.82123(1) nm3, Z = 2, Mr = 852.56, F(000) = 1862, Dc = 1.555 g cm-3, μ(M0Ka) = 1.056 mm-1. It turned out that six oxygen atoms from three nirtate anions, one oxygen atom in ethanol and two phenolate oxygen atoms from two Schiff base ligands coordinate to La(III), forming a 9-coordination distorted monocapped square prism geometry. In addition, DNA-binding of the complex was studied by EtBr fluoescent probe and the results show that the complex interact with DNA by intercalative mode. CCDC:878971.

  由硝酸镧和希夫碱（C15H15NO2，由邻香兰素和对甲苯胺衍生而来）在乙醇中回流合成了一种新的配合物[La(NO3)3(C2H5OH)(C15H15NO2)2]。其晶体结构是通过单晶 X 射线衍射法测定的。该复合物为三菱晶体，空间群为 P-1，a = 0.79851(3) nm，b = 1.47473(5) nm，c = 1.63872(6) nm，a = 73.546(2)º， b = 86.769(2)º， g = 79.767(2)º，V = 1.82123(1) nm3，Z = 2，Mr = 852.56，F(000) = 1862，Dc = 1.555 g cm-3，μ(M0Ka) = 1.056 mm-1。结果表明，三个镍酸根阴离子中的六个氧原子、乙醇中的一个氧原子和两个希夫碱配体中的两个苯酚氧原子与 La(III)配位，形成了一个 9 配位畸变单帽方棱几何结构。此外，还利用 EtBr 荧光探针研究了该配合物与 DNA 的结合，结果表明该配合物通过插层模式与 DNA 发生相互作用。CCDC:878971.