N-(5-bromosalicylidene)-2-chloroaniline | 89046-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(5-bromosalicylidene)-2-chloroaniline
• 英文别名: Phenol, 4-bromo-2-[[(2-chlorophenyl)imino]methyl]-；4-bromo-2-[(2-chlorophenyl)iminomethyl]phenol
• CAS: 89046-29-7
• 化学式: C₁₃H₉BrClNO
• 分子量: 310.578
• InChiKey: JTZYREHINFJETQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：

  N-(5-bromosalicylidene)-2-chloroaniline 在 sodium tetrahydroborate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 1-(5-bromo-2-hydroxybenzyl)-1-(2-chlorophenyl)-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：

  邻氯苯胺 、 5-溴水杨醛 以 乙醇 为溶剂， 以65%的产率得到N-(5-bromosalicylidene)-2-chloroaniline
  参考文献：
  名称：

  甲基三氧杂hen催​​化的拟枯烯氧化用于维生素E合成：溶剂和配体效应的研究

  摘要：

  维生素E是具有重要抗氧化剂特性和生物活性的，具有重要经济意义的重要食品成分。假异丙苯氧化为三甲基-1,4-苯醌将是α-生育酚替代工业生产中的关键转变，这对维生素E的抗氧化活性很重要。甲基三氧杂（（MTO）催化的假异丙苯氧化已被重新研究为这种重要的工业产品提供更环保，更经济和更温和的方法。已经观察到，通过选择溶剂和路易斯碱添加剂（作为MTO的配体），产率和化学选择性都得到了显着提高，与先前报道的方案相比，允许较温和的反应条件。

  DOI：

  10.1016/j.jcat.2011.07.003

文献信息

• Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin E synthesis: A study of solvent and ligand effects
  作者：Mónica Carril、Philipp Altmann、Markus Drees、Werner Bonrath、Thomas Netscher、Jan Schütz、Fritz E. Kühn

  DOI：10.1016/j.jcat.2011.07.003

  日期：2011.10

  Vitamin E is an essential food component of major economical relevance with important antioxidant properties and biological activity. The oxidation of pseudocumene to trimethyl-1,4-benzoquinone would be a key transformation in an alternative industrial production of α-tocopherol that is important for the antioxidant activity of vitamin E. The methyltrioxorhenium (MTO)-catalyzed oxidation of pseudocumene

  维生素E是具有重要抗氧化剂特性和生物活性的，具有重要经济意义的重要食品成分。假异丙苯氧化为三甲基-1,4-苯醌将是α-生育酚替代工业生产中的关键转变，这对维生素E的抗氧化活性很重要。甲基三氧杂（（MTO）催化的假异丙苯氧化已被重新研究为这种重要的工业产品提供更环保，更经济和更温和的方法。已经观察到，通过选择溶剂和路易斯碱添加剂（作为MTO的配体），产率和化学选择性都得到了显着提高，与先前报道的方案相比，允许较温和的反应条件。
• Halide substituted Schiff-bases: Different activities in methyltrioxorhenium(VII) catalyzed epoxidation via different substitution patterns
  作者：Philipp Altmann、Mirza Cokoja、Fritz E. Kühn

  DOI：10.1016/j.jorganchem.2011.12.010

  日期：2012.3

  influence of halide substituted Schiff-bases as ligands of methyltrioxorhenium (MTO) in epoxidation catalysis. Therefore, selected Schiff-bases were prepared by the reaction of hydroxy-benzaldehydes and aniline derivates. These differently substituted Schiff-bases were tested as MTO-ligands in cyclooctene- and 1-octene-epoxidation. Although no great disparities among the substitution patterns have been

  该报告显示了卤化物取代的席夫碱作为甲基三氧or（MTO）配体在环氧化催化中的影响。因此，通过羟基苯甲醛与苯胺衍生物的反应制备了选定的席夫碱。这些不同取代的席夫碱已作为环辛烯和1-辛烯环氧化的MTO配体进行了测试。尽管没有发现替换模式之间的巨大差异，但可以得出一些结论。氟草胺的替代品不及氯或溴。邻位卤化物的活性高于对位或间位卤化物-位置。在Schiff碱处，给电子和吸电子的影响之间的平衡在环氧化催化中用作MTO的配体方面起着重要作用。
• Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors
  作者：Zi-Lin Li、Qing-Shan Li、Hong-Jia Zhang、Yang Hu、Di-Di Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.06.049

  日期：2011.8

  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.