N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-bromobenzaldimine | 137532-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-bromobenzaldimine
• 英文别名: 4-bromo-2-((2-hydroxy-5-methylphenylimino)methyl)phenol；4-bromo-2-{(2-hydroxy-5-methylphenyl)iminomethyl}phenol；N-(5-methyl-2-hydroxyphenyl)-5-bromosalicylaldimine；4-Bromo-2-{[(2-hydroxy-5-methylphenyl)imino]methyl}phenol；2-[(5-bromo-2-hydroxyphenyl)methylideneamino]-4-methylphenol
• CAS: 137532-62-8
• 化学式: C₁₄H₁₂BrNO₂
• 分子量: 306.159
• InChiKey: BGCFQQJFYQUETE-UHFFFAOYSA-N

物化性质

• 沸点：
  488.0±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-bromobenzaldimine 、 bis(2,4-pentanedionato)dioxomolybdenum(VI) 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到
  参考文献：
  名称：

  一种新的钼席夫碱配合物作为具有极高周转数的环氧化催化剂的合成、结构表征和研究

  摘要：

  摘要 [MoO2(acac)2]与ONO型席夫碱配体(L = 4-bromo-2-((2-hydroxy-5-methylphenylimino)methyl)phenol)反应生成了一种新的低聚物钼配合物([ MoO2(L)]n)。低聚物配合物通过元素分析、FT-IR、1H和13C NMR光谱表征。该复合物的合适单晶在 DMSO 中生长，并通过 X 射线单晶衍射表征为由一个 DMSO 分子 [MoO2L(DMSO)] 稳定的单体。[MoO2(L)]n 络合物用作烯烃环氧化反应的催化剂。除了高活性和选择性之外，非常高的转换数是催化系统的显着优势。

  DOI：

  10.1016/j.inoche.2017.07.025
• 作为产物：
  描述：

  邻氨基对甲苯酚 、 5-溴水杨醛 以 乙醇 为溶剂， 反应 3.0h， 以73%的产率得到N-(5-methyl-2-hydroxyphenyl)-2-hydroxy-5-bromobenzaldimine
  参考文献：
  名称：

  某些4-甲基-2-氨基苯酚衍生的席夫碱的光谱表征和抗菌活性

  摘要：

  使用适当的合成路线合成了一系列N-（5-甲基-2-羟基苯基）-（2/3/4 / 5-取代）-苯甲二胺（I – XIII）。它们的结构通过FT-IR，UV-Visible，ESI-MS，1 H和13 C-NMR光谱技术和分析方法来表征。N-（5-甲基-2-羟基苯基）-3,4-二甲氧基苯甲二胺（XIII）的晶体结构在室温下通过X射线衍射测定。研究了熔点与化合物结构之间的关系。评价了该化合物对金黄色葡萄球菌，表皮葡萄球菌的抗菌活性。，大肠杆菌，肺炎克雷伯菌，铜绿假单胞菌和奇异变形杆菌。据报道，白色念珠菌具有抗真菌活性。一些席夫碱的表现出了相当的抗菌活性对金黄色葡萄球菌和Ç。白色的。

  DOI：

  10.1002/cjoc.201100237

文献信息

• Spectral Characterization and Antimicrobial Activity of Some Schiff Bases Derived from 4-Methyl-2-aminophenol
  作者：Demet Gürbüz、Adem Cinarli、Aydin Tavman、A. Seher Birteksz

  DOI：10.1002/cjoc.201100237

  日期：2012.4

  the compounds were examined. Antibacterial activities of the compounds were evaluated against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Proteus mirabilis. Antifungal activities were reported for Candida albicans. Some of the Schiff bases showed considerable antimicrobial activity against S. aureus and C. albicans.

  使用适当的合成路线合成了一系列N-（5-甲基-2-羟基苯基）-（2/3/4 / 5-取代）-苯甲二胺（I – XIII）。它们的结构通过FT-IR，UV-Visible，ESI-MS，1 H和13 C-NMR光谱技术和分析方法来表征。N-（5-甲基-2-羟基苯基）-3,4-二甲氧基苯甲二胺（XIII）的晶体结构在室温下通过X射线衍射测定。研究了熔点与化合物结构之间的关系。评价了该化合物对金黄色葡萄球菌，表皮葡萄球菌的抗菌活性。，大肠杆菌，肺炎克雷伯菌，铜绿假单胞菌和奇异变形杆菌。据报道，白色念珠菌具有抗真菌活性。一些席夫碱的表现出了相当的抗菌活性对金黄色葡萄球菌和Ç。白色的。
• Synthesis, X-ray crystal structure, DFT calculation and catalytic activity of two new oxido-vanadium(V) complexes containing ONO tridentate Schiff bases
  作者：S. Yousef Ebrahimipour、Mehdi Abaszadeh、Jesús Castro、Mohammad Seifi

  DOI：10.1016/j.poly.2014.04.069

  日期：2014.9

  Two new oxido-vanadium(V) complexes, [VO(L-1)(EtO)] (1) and [VO(L-2)(2-BuO)] (2) [H2L1 = 2(5-chloro-2-hydroxyphenyl)iminomethyl}phenol and H2L2 = 4-bromo-2-(2-hydroxy-5-methylphenyl] iminomethyl}phenol], have been prepared by the reaction of VO(acac)(2) with the ONO tridentate salicylidene Schiff bases H2L1 and H2L2, and fully characterized by FT-IR, molar conductivity, elemental analyses, H-1 NMR and electronic spectra. The structures of the complexes have also been determined by X-ray diffraction. Computational studies were performed at the B3LYP/6-311G(d,p) level. Furthermore, the catalytic activity of these compounds was investigated for a multicomponent reaction of cyclic enaminoketones, malononitrile and aromatic aldehydes. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, structure characterization and study of a new molybdenum Schiff base complex as an epoxidation catalyst with very high turnover numbers
  作者：Mojtaba Bagherzadeh、Saeed Ataie、Hamed Mahmoudi、Jan Janczak

  DOI：10.1016/j.inoche.2017.07.025

  日期：2017.10

  Abstract The reaction between [MoO2(acac)2] and an ONO type Schiff-base ligand (L = 4-bromo-2-((2-hydroxy-5-methylphenylimino)methyl)phenol) resulted a new oligomer molybdenum complex ([MoO2(L)]n). The oligomer complex was characterized by elemental analysis, FT-IR, 1H and 13C NMR spectroscopies. A suitable single crystal of the complex was grown in DMSO and characterized by X-ray single crystal diffraction

  摘要 [MoO2(acac)2]与ONO型席夫碱配体(L = 4-bromo-2-((2-hydroxy-5-methylphenylimino)methyl)phenol)反应生成了一种新的低聚物钼配合物([ MoO2(L)]n)。低聚物配合物通过元素分析、FT-IR、1H和13C NMR光谱表征。该复合物的合适单晶在 DMSO 中生长，并通过 X 射线单晶衍射表征为由一个 DMSO 分子 [MoO2L(DMSO)] 稳定的单体。[MoO2(L)]n 络合物用作烯烃环氧化反应的催化剂。除了高活性和选择性之外，非常高的转换数是催化系统的显着优势。
• Synthesis, spectral characterization, DFT calculations, antimicrobial activity and molecular docking of 4-bromo-2-((2-hydroxy-5-methylphenylimino)methyl)phenol and its V(V) complex
  作者：Reza Takjoo、Alireza Akbari、S. Yousef Ebrahimipour、Maciej Kubicki、Maryam Mohamadi、Nasrin Mollania

  DOI：10.1016/j.ica.2016.10.018

  日期：2017.1

  VO(acac)(2) reacted with a new ONO tridentate Schiff base, 4-bromo-2-((2-hydroxy-5-methylphenylimino) methyl)phenol, (H2L) in methanol to afford a new V(V) complex, [VO(L)(MeO)(MeOH)]. Characterization by elemental analysis, molar conductivity, FT-IR, electronic spectroscopy, H-1 NMR, single crystal X-ray and TGA studies indicated that the free ligand existed as its keto tautomer in solid state, while in the complex it was coordinated to the regular VO core in its deprotonated form (enol), as a tridentate anionic ligand. The vanadium center was also found to be 6-coordinated, in a distorted octahedral fashion with a deprotonated ligand and an oxygen atom of the methoxy group in the equatorial plane and an oxido ligand and an oxygen from methanol in the apical sites. DFT and NBO calculations were additionally performed and confirmed the experimental data. The synthesized ligand and its oxido-vanadium(V) complex exhibited satisfactory antimicrobial activities against some tested Gram-positive and Gram-negative bacteria, and fungus strain. In addition, the potential of these compounds as antimicrobial agents was investigated using molecular docking to glucosamine-6-phosphate (GlcN-6-P) synthase. (C) 2016 Elsevier B.V. All rights reserved.