5-bromo-salicylidene-4-bromoaniline | 93186-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-bromo-salicylidene-4-bromoaniline
• 英文别名: 4-bromo-2-[(4-bromophenylimino)methyl]phenol；5-Brom-salicylaldehyd-<4-brom-phenylimin>；5-Brom-2-hydroxy-benzaldehyd-(4-brom-phenylimin)；4-Brom-2-[(4-brom-phenylimino)-methyl]-phenol；4-Bromo-2-[(E)-[(4-bromophenyl)imino]methyl]phenol；4-bromo-2-[(4-bromophenyl)iminomethyl]phenol
• CAS: 93186-78-8
• 化学式: C₁₃H₉Br₂NO
• mdl: MFCD00297487
• 分子量: 355.029
• InChiKey: WBJGMDBPWOVGSW-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C(Solv: ethanol (64-17-5))
• 沸点：
  444.1±45.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-salicylidene-4-bromoaniline 在 sodium tetrahydroborate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 1-(5-bromo-2-hydroxybenzyl)-1-(4-bromophenyl)-3-phenylurea
  参考文献：
  名称：

  Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors

  摘要：

  FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of o-hydroxybenzylamines 1-16 and its corresponding new urea derivatives 17-32 were synthesized and fully characterized by spectroscopic methods and elemental analysis. This new urea derivatives class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-bromo-2-hydroxybenzyl)-1-(4-fluorophenyl)-3-phenylurea (18) and 1-(5-bromo-2-hydroxybenzyl)-1-(4-chlorophenyl)-3-phenylurea (20) were potent inhibitors of E. coli FabH. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.049
• 作为产物：
  描述：

  水杨醛 在 四氯化碳 、 溴 作用下， 生成 5-bromo-salicylidene-4-bromoaniline
  参考文献：
  名称：

  Phototropic and Thermotropic Anils from 5-Bromosalicylaldehyde

  摘要：

  DOI：

  10.1021/ja01329a049

文献信息

• Qualitative Analysis of the Stability of the Oxazine Ring of Various Benzoxazine and Pyridooxazine Derivatives with Proton Nuclear Magnetic Resonance Spectroscopy
  作者：Gerard P. Moloney、David J. Craik、Magdy N. Iskander

  DOI：10.1002/jps.2600810721

  日期：1992.7

  3-benzoxazine and 3,4-dihydro-1,3-pyridooxazine derivatives was synthesized, and the hydrolysis of the derivatives was studied with proton nuclear magnetic resonance spectroscopy. The oxazine derivatives underwent various degrees of hydrolysis when H2O was added to dimethyl sulfoxide solutions of the compounds. The rates and extents of decomposition of the oxazine ring systems depended on the electronic effects

  合成了一系列的3,4-二氢-1,3-苯并恶嗪和3,4-二氢-1,3-吡啶并恶嗪衍生物，并利用质子核磁共振波谱研究了这些衍生物的水解。当将H 2 O加入到化合物的二甲基亚砜溶液中时，恶嗪衍生物经历了不同程度的水解。恶嗪环系统分解的速率和程度取决于分子内取代基的电子效应。对恶嗪分解期间产生的质子核磁共振谱以及恶嗪衍生物的稳定性趋势的研究表明在水解机理中形成了中间体。
• Brønsted acids of anionic chiral Co(<scp>iii</scp>) complexes as catalysts for the stereoselective synthesis of cis-4-aminofuranobenzopyrans
  作者：Hua-Jie Jiang、Kun Liu、Jing Wang、Na Li、Jie Yu

  DOI：10.1039/c7ob02452e

  日期：——

  A highly enantioselective interrupted Povarov reaction of salicylaldimines and 2,3-dihydrofuran was developed, through the elegant Brønsted acid catalysis of anionic chiral Co(III) complexes. This reaction affords the cis-4-aminofuranobenzopyran derivatives with up to 95% yield, >20:1 dr and 96:4 er. Moreover, a one-pot three-component procedure of salicylaldehydes, anilines, and 2,3-dihydrofuran proves

  通过优雅的布朗斯台德酸催化阴离子手性Co（III）配合物，开发了水杨醛亚胺和2,3-二氢呋喃的高度对映选择性中断Povarov反应。该反应以高达95％的产率，> 20：1 dr和96：4 er提供了顺式-4-氨基呋喃并苯并吡喃衍生物。而且，水杨醛，苯胺和2，3-二氢呋喃的一锅三组分法被证明是成功的，具有更高的反应效率。
• Vanadyl Binary Schiff Base Complexes Containing N₂O₂Coordination Sphere: Synthesis, Ab Initio Calculations and Thermodynamic Properties
  作者：Mozaffar Asadi、Mohammad Hadi Ghatee、Susan Torabi、Khosro Mohammadi、Fatemeh Moosavi

  DOI：10.5012/jkcs.2013.57.1.63

  日期：2013.2.20

  Some vanadyl complexes were synthesized by treating a methanolic solution of the appropriate Schiff base ligand and one equivalent of $VO(SO_4)_2$ to yield [($VOL_2^1-14}$)](L=Salicylaldehyde's derivatives, Schemes 1, 2). These oxovanadium (IV) complexes were characterized based on their FT-IR, UV-Vis spectroscopy and elemental analysis. The IR spectra suggest that coordination takes place through azomethine nitrogen and phenolate oxygen. In addition, the formation constants of the oxovanadium (IV) binary complexes were determined in methanolic medium. The ab initio calculations were also carried out to determine the structural and the geometrical properties of one of the complexes and its calculated vibrational frequencies were investigated.

  一些钒氧配合物是通过将适当的水杨醛衍生物希夫碱配体和等量的$VO(SO_4)_2$溶于甲醇溶液中合成的，生成[(VOL_2^1-14})](L=水杨醛衍生物，方案1、2)。这些四价氧化钒配合物根据其FT-IR、UV-Vis光谱和元素分析进行了表征。红外光谱表明配位通过偶氮甲碱氮和酚氧发生。此外，四价氧化钒二元配合物在甲醇介质中的形成常数也被测定。还进行了从头计算，以确定其中一个配合物的结构和几何性质及其计算的振动频率。
• Novel copper(II) and zinc(II) complexes of halogenated bidentate N,O-donor Schiff base ligands: Synthesis, characterization, crystal structures, DNA binding, molecular docking, DFT and TD-DFT computational studies
  作者：Hadi Kargar、Reza Behjatmanesh-Ardakani、Vajiheh Torabi、Asiyehalsadat Sarvian、Zahra Kazemi、Zahra Chavoshpour-Natanzi、Valiollah Mirkhani、Atefeh Sahraei、Muhammad Nawaz Tahir、Muhammad Ashfaq

  DOI：10.1016/j.ica.2020.120004

  日期：2021.1

  bidentate N,O-donor halogenated bis-Schiff base ligands (HL1: 4-Bromo-2-[(4-fluorophenylimino) methyl]phenol; HL2: 4-Bromo-2-[(4-chlorophenylimino)methyl]phenol; HL3: 4-Bromo-2-[(4-bromophenylimino) methyl]phenol; HL4: 4-Bromo-2-[(4- iodophenylimino)methyl]phenol) were synthesized and their structures were proved by SC-XRD, FT-IR, UV-Vis, and 1H NMR spectroscopic techniques. The single crystal X-ray diffraction

  摘要八个新颖的配合物，包括：[Cu（L1）2]：C1，[Cu（L2）2]：C2，[Cu（L3）2]：C3，[Cu（L4）2]：C4，[Zn（ L1）2]：Z1，[Zn（L2）2]：Z2，[Zn（L3）2]：Z3和[Zn（L4）2]：Z4，带有四个双齿N，O-施主卤代双席夫碱性配体（HL1：4-溴-2-[（4-氟苯基亚氨基）甲基]苯酚; HL2：4-溴-2-[（4-氯苯基亚氨基）甲基]苯酚; HL3：4-溴-2-[[4 -溴苯基亚氨基）甲基]苯酚；合成了HL4：4-溴-2-[（4-碘苯基亚氨基）甲基]苯酚），并通过SC-XRD，FT-IR，UV-Vis和1H NMR光谱技术证实了它们的结构。单晶X射线衍射分析表明，在锌络合物中形成了扭曲的四面体几何形状，而在C3和C4的铜（II）络合物中都形成了略微扭曲的正方形平面几何形状。使用Def2-TZVP基集，使用B3LYP方法通过DFT和TD-DF
• Aza-Diels–Alder Reactions with Lanthanide Triflates: Syntheses of Quinoline and Phenanthridine Derivatives
  作者：Kadir Turhan、Emel Pelit、Zuhal Turgut

  DOI：10.1080/00397910802585902

  日期：2009.4.22

  The aza-Diels-Alder reactions of cyclopentadiene and cyclo-1,3-hexadiene with various substituted N-arylimines in the presence of Yb/Sc triflates as catalyst in MeCN at room temperature gave quinoline and phenanthridine derivatives in moderate to high yields. Some of the cycloaddition reactions were carried out in ionic liquid.