N-(2-hydroxy-5-bromobenzylidene)-4-methylaniline | 20772-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2-hydroxy-5-bromobenzylidene)-4-methylaniline
• 英文别名: 4-bromo-2-(p-tolylimino-methyl)-phenol；5-Brom-2-hydroxy-benzaldehyd-p-tolylimin；4-Brom-2-(p-tolylimino-methyl)-phenol；N-<5-Brom-salicyliden>-p-toluidin；5-Brom-4'-methyl-salicyliden-anilin；4-bromo-2-{(E)-[(4-methylphenyl)imino]methyl}phenol；4-bromo-2-[(4-methylphenyl)iminomethyl]phenol
• CAS: 20772-74-1
• 化学式: C₁₄H₁₂BrNO
• 分子量: 290.159
• InChiKey: CVLPUORVUJWTIO-UHFFFAOYSA-N

物化性质

• 沸点：
  414.8±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(2-hydroxy-5-bromobenzylidene)-4-methylaniline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-bromo-2-((p-tolylamino)methyl)phenol
  参考文献：
  名称：

  A Quick Route for the Synthesis of 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-ones

  摘要：

  N-(2-羟基)-苄基-芳香胺（1）在20-25 ºC的DMSO中与碳酰二咪唑环化，20-30分钟后获得了3-芳基-3,4-二氢-2H-benz[e]-1,3-噁唑啉-2-酮（2），产率非常高。

  DOI：

  10.14233/ajchem.2013.14053
• 作为产物：
  描述：

  水杨醛 在 四氯化碳 、 乙醇 、 溴 作用下， 生成 N-(2-hydroxy-5-bromobenzylidene)-4-methylaniline
  参考文献：
  名称：

  Phototropic and Thermotropic Anils from 5-Bromosalicylaldehyde

  摘要：

  DOI：

  10.1021/ja01329a049

文献信息

• A stereoselective synthesis of symmetrical and unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives induced by low-valent titanium reagent
  作者：Guo-Lan Dou、Fang Sun、Da-Qing Shi

  DOI：10.1016/j.tet.2012.03.122

  日期：2012.6

  unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives were synthesized by the reaction of various o-hydroxy Schiff bases and triphosgene induced by low-valent titanium reagent (TiCl4/Sm). A variety of substrates can participate in the process with good yields. The present method provides a useful preparation of 3,3′,4,4′-tetrahydro-4,4′-bibenzo[e][1,3]oxazine-2,2′-dione derivatives, which cannot be

  低价钛试剂（TiCl 4 / Sm）诱导的各种邻羟基席夫碱与三光气反应合成了一系列对称和不对称的联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物。）。多种底物可以高收率参与该过程。本方法提供了有用的3,3'，4,4'-四氢-4,4'-联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物的制备方法，否则无法制备。反应的机理表明一锅参与还原，偶联和环化。
• Cation-/Ligand-Induced Solvent-Assisted Transformations of Zn(II) and Cu(II) Complexes Featuring Single-Pocket Multidentate Chelating Members
  作者：Siya T. Hulushe、Frederick P. Malan、Eric C. Hosten、Matthew P. Akerman、Andreas Lemmerer、Setshaba D. Khanye、Gareth M. Watkins

  DOI：10.1021/acs.cgd.3c00055

  日期：2023.7.5

  starting from synthesized and fully characterized Zn(II) (1a; I2/a) and Cu(II) (2a; C2) precursors, were conveniently prepared via cation-induced solvent-assisted and ligand-induced solvent-assisted transformations. Herein, we show multistep solvent-assisted transformations from cis-1a → trans-1b → cis-1c → cis-1d, as well as all-trans 2a → 2b → 2c. All processes are one-way irreversible, as substantiated

  带有O,N,O-三齿和O,N-二齿螯合成员的新单口袋金属配合物家族Cu, 1b ( P 2 1 / n ); Ni，1c ( C 2/ c )；Mn，1d（I 2/ a）；铜，2b；和 Ni, 2c（均为P 2 1 / c）}，从合成并完全表征的 Zn(II) ( 1a ; I 2/ a ) 和 Cu(II) ( 2a ; C 2）前体，可以通过阳离子诱导的溶剂辅助和配体诱导的溶剂辅助转化方便地制备。在这里，我们展示了从cis - 1a → trans - 1b → cis - 1c → cis - 1d以及全反式 2a → 2b → 2c的多步溶剂辅助转化。所有过程都是单向不可逆的，正如密度泛函理论计算得出的热力学方面（基于吉布斯自由能的热函）所证实的那样。另一方面，复数2a′ ( C 2/ c; 通过常规合成程序获得2a )的多晶型。这些化合物是通过各种光谱技术（红外、紫外-可见、ESI-MS、1
• Mayadeo, M. S.; Nalgirkar, Jyoti V., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 5, p. 456 - 457
  作者：Mayadeo, M. S.、Nalgirkar, Jyoti V.

  DOI：——

  日期：——
• 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.
• Reformatsky Reaction of Methyl α-Bromoisobutyrate with Schiff Bases Derived from Salicylaldehyde and 2-Hydroxynaphthalene-1-carbaldehyde
  作者：V. V. Shchepin、D. V. Fotin、M. I. Vakhrin

  DOI：10.1023/b:rujo.0000044546.25792.5b

  日期：2004.6

  Reformatsky reaction of methyl alpha-bromoisobutyrate with Schiff bases derived from salicylaidehyde and its analogs gives the corresponding 1,4-disubstituted 3,3-dimethylazetidin-2-ones.