2-{(5-氯-2-羟基苯基)亚氨基甲基}苯酚 | 111200-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-{(5-氯-2-羟基苯基)亚氨基甲基}苯酚
• 英文名称: 2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol
• 英文别名: 2-{(5-chloro-2-hydroxyphenyl)iminomethyl}phenol；salicylidene-(5-chloro-2-hydroxy-aniline)；N-salicylidene-4-chloro-o-aminophenol；4-chloro-2-salicylidenamino-phenol；Salicylaldehyd-(5-chlor-2-hydroxy-phenylimin)；4-Chlor-2-salicylidenamino-phenol；alpha-(5-Chloro-2-hydroxyphenylimino)-O-cresol；4-chloro-2-[(2-hydroxyphenyl)methylideneamino]phenol
• CAS: 111200-04-5；1761-31-5
• 化学式: C₁₃H₁₀ClNO₂
• 分子量: 247.681
• InChiKey: MECAZNFEEJTGNK-UHFFFAOYSA-N

物化性质

• 沸点：
  465.2±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 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：

  2-{(5-氯-2-羟基苯基)亚氨基甲基}苯酚 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 2-(5-chlorobenzoxazol-2-yl)phenol
  参考文献：
  名称：

  第4种族配合物的配体salicylbenzoxazole作为有效催化剂的丙交酯，环氧化物的开环聚合和共聚的ε与己内酯大号丙交酯

  摘要：

  使一系列水杨基苯并恶唑原配体2-（5-X-苯并恶唑-2-基）-6-R 1 -4-R 2-苯酚L 1 H-L 4 H与钛，锆和ha的醇盐反应。存在于配体前骨中的取代基（R 1，R 2，X）为L1H的（H，H，H）；（H，H，Cl）为L2H ; L3H的（Br，Br，H）; L4H的（Cl，Cl，H）和。通过将原配体L1H-L4H与Ti（O i Pr）结合制备[M（L）2（O i Pr）2 ]制剂的单核Ti配合物1a-4a4在无水甲苯中。但是，通过添加H 2 O（0.5 M当量），在THF /甲苯混合溶剂中控制Ti络合物4a的水解，生成具有[M（μ-O）（L）的氧桥联双核Ti络合物5a。2（O i Pr）] 2配方使用L4H作为原配体，收率良好（≥75％）。发现L1H-L4H的单核Zr和Hf配合物的组成与Ti配合物的组成非常相似。另外，制备单核Zr复合物1b-4b和Hf复合物1c-4c。氧桥双

  DOI：

  10.1016/j.polymer.2016.08.007
• 作为产物：
  描述：

  水杨醛 、 邻氨基对甲苯酚 以 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到2-{(5-氯-2-羟基苯基)亚氨基甲基}苯酚
  参考文献：
  名称：

  Synthesis, X-ray crystal structure, DFT calculation and catalytic activity of two new oxido-vanadium(V) complexes containing ONO tridentate Schiff bases

  摘要：

  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.

  DOI：

  10.1016/j.poly.2014.04.069

文献信息

• Construction of functionalized 2,3-dihydro-1,4-benzoxazines via [5 + 1] annulations of 2-halo-1,3-dicarbonyl compounds with imines
  作者：Ya-Ru Zhang、Jian-Wu Xie、Xu-Jiao Huang、Wei-Dong Zhu

  DOI：10.1039/c2ob25927c

  日期：——

  A series of functionalized 2,3-dihydro-1,4-benzoxazines were obtained in moderate to excellent yields via domino [5 + 1] annulations of 2-halo-1,3-dicarbonyl compounds 2 with imines 1 under mild conditions and the application of this method in the synthesis of bioactive analogues, such as functionalized tetracyclic-1,4-benzoxazines which contain two new heterocyclic rings and one quaternary carbon

  在中度得到以优异的产率的一系列官能化2,3-二氢-1,4-苯并恶嗪的经由多米诺[5 + 1] 2-卤代-1,3-二羰基的化合物annulations 2与亚胺1温和的条件和所述下还开发了该方法在生物活性类似物合成中的应用，例如含有两个新的杂环和一个季碳中心的功能化四环-1,4-苯并恶嗪。
• Synthesis, spectroscopy, electrochemistry and thermal study of vanadyl tridentate Schiff base complexes
  作者：Ali Hossein Kianfar、Marzeh Paliz、Mahmoud Roushani、Mojtaba Shamsipur

  DOI：10.1016/j.saa.2011.06.058

  日期：2011.11

  The VO(IV) complexes of tridentate ONO Schiff ligands were synthesised and characterized by IR, UV–vis and elemental analysis. The electrochemical properties of the vanadyl complexes were investigated by cyclic voltammetry. A good correlation was observed between the oxidation potentials and the electron withdrawing character of the substituents on the Schiff base ligands, showing the following trend:

  合成了三齿ONO Schiff配体的VO（IV）配合物，并通过IR，UV-vis和元素分析对其进行了表征。通过循环伏安法研究了钒基配合物的电化学性质。席夫碱配体上的取代基的氧化电势与吸电子特性之间存在良好的相关性，表现出以下趋势：MeO
• Imino Diels–Alder reaction of boronates: A new route to 3,4-dihydroquinolines
  作者：Mario Rodríguez、Ma. Eugenia Ochoa、Rosa Santillan、Norberto Farfán、Victor Barba

  DOI：10.1016/j.jorganchem.2005.03.024

  日期：2005.6

  The synthesis of a series of 3,4-dihydroquinolines (3b–e, 3h and 3i) by Imino Diels–Alder reactions involving sulfolene and boronates 2a–j derived from Schiff bases is described. The reactions are regioselective leading to 4-substituted dihydroquinolines with a cis relative stereochemistry between the phenyl group on the boron atom and the vinyl substituent at position 4, as established by X-ray diffraction

  描述了通过Imino Diels-Alder反应合成的一系列3,4-二氢喹啉（3b – e，3h和3i），其中涉及亚砜和席夫碱衍生的硼酸酯2a – j。该反应是区域选择性的，导致4-取代的二氢喹啉，其在硼原子上的苯基与4位上的乙烯基取代基之间具有顺式相对立体化学，如通过3b，3e，3h和3i的X射线衍射分析所建立的。
• Spectral Characterization and Antimicrobial Activity of Some Schiff Bases Derived from 4-Chloro-2-aminophenol and Various Salicylaldehyde Derivatives
  作者：Adem Cinarli、Demet Gürbüz、Aydin Tavman、A. Seher Birteksöz

  DOI：10.1002/cjoc.201180473

  日期：2012.2

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

  使用适当的合成路线合成了一系列N-（5-氯-2-羟基苯基）-（3/4 / 5-取代）-水杨醛亚胺（I - XI）。通过FT-IR，UV-Visible，ESI-MS，1 H和13 C NMR光谱技术和分析方法对它们的结构进行了表征。N-（5-氯-2-羟基苯基）-5-溴水杨基醛亚胺（V）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。评估了该化合物对金黄色葡萄球菌，表皮葡萄球菌，大肠杆菌，肺炎克雷伯菌，铜绿假单胞菌，奇异变形杆菌。据报道，白色念珠菌具有抗真菌活性。席夫碱表现出了相当的抗菌活性对金黄色葡萄球菌，表皮葡萄球菌和Ç。白色的。N-（5-氯-2-羟基苯基）-3-羟基水杨基亚胺（II）具有最广泛和最高的抗菌活性。
• Syntheses, characterizations, crystal structures, and biological activities of two new mixed ligand Ni(II) and Cu(II) Schiff base complexes
  作者：S. Yousef Ebrahimipour、Maryam Mohamadi、Jesús Castro、Nasrin Mollania、Hadi Amiri Rudbari、Alessandro Saccá

  DOI：10.1080/00958972.2014.1000883

  日期：2015.2.16

  imidazole. Their structures were characterized by microanalysis, FT-IR, UV–vis, molar conductivity, and 1H NMR for [Ni(L)(2imi)]·MeOH. The structures were determined using single crystal X-ray diffraction. Each four-coordinate metal center, Cu(II) in 1 and Ni(II) in 2, is surrounded by donors of Schiff base (L2−) and N of 2-methyl imidazole in square planar geometries. α-Amylase activities of these compounds

  两种混合配体配合物，[Cu(L)(2imi)] (1) 和 [Ni(L)(2imi)]·MeOH (2) [L = 2-(((5-chloro-2-oxyphenyl)imino )methyl)phenolato) 和 2imi = 2-甲基咪唑]，已通过适当的金属盐与 H2L 和 2-甲基咪唑反应制备。它们的结构通过[Ni(L)(2imi)]·MeOH的微量分析、FT-IR、UV-vis、摩尔电导率和1H NMR表征。使用单晶X射线衍射确定结构。每个四配位金属中心，即 1 中的 Cu(II) 和 2 中的 Ni(II)，被席夫碱 (L2-) 的供体和 2-甲基咪唑的 N 以方形平面几何形状包围。还研究了这些化合物的α-淀粉酶活性。实验数据表明，α-淀粉酶被 Ni(II) 复合物抑制，而 Cu(II) 复合物导致 Km 值下降 1.3 倍。