4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol | 325471-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol
• 英文别名: 4-bromo-2-[(2-fluorophenyl)iminomethyl]phenol
• CAS: 325471-45-2
• 化学式: C₁₃H₉BrFNO
• mdl: MFCD01849311
• 分子量: 294.123
• InChiKey: XFARSEXTBJQNRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol 在 sodium tetrahydroborate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 1-(5-bromo-2-hydroxybenzyl)-1-(2-fluorophenyl)-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：

  2-氟苯胺 、 5-溴水杨醛 以 乙醇 为溶剂， 生成 4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol
  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

文献信息

• Asymmetric Synthesis of 3,4-Diaminochroman-2-ones Promoted by Guanidine and Bisguanidium Salt
  作者：Shunxi Dong、Xiaohua Liu、Yulong Zhang、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol2018888

  日期：2011.10.7

  A highly enantioselective synthesis of 3,4-diaminochroman-2-ones has been realized via the domino reaction of o-hydroxy aromatic aldimines and azlactones. Notably, a cis-product was obtained as the major product by the use of guanidine 2a whereas a trans-product was the major product with bisguanidium salt 3•HBArF4. In two cases, various substituted 3,4-dihydrocoumarins were obtained with high yields

  通过邻羟基芳族醛亚胺和a内酯的多米诺反应，已经实现了对3,4-二氨基苯并二氢吡喃-2-酮的高度对映选择性的合成。值得注意的是，通过使用胍2a获得了顺式产物作为主要产物，而反式产物是双胍盐3•HBAr F 4的主要产物。在两种情况下，以高收率（高达99％），出色的对映选择性（高达99％ee）和非对映选择性（高达> 99：1顺式：反式和98：2 ）获得了各种取代的3,4-二氢香豆素。反式：顺式，分别）在温和的反应条件下。
• 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.