5-bromo-salicylidene-4-methoxyaniline | 20772-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-salicylidene-4-methoxyaniline
• 英文别名: 5-bromosalicylidene-p-anisidine；4-bromo-2-[(4-methoxy-phenylimino)-methyl]-phenol；4-Brom-2-[(4-methoxy-phenylimino)-methyl]-phenol；5-Brom-2-hydroxy-benzaldehyd-(4-methoxy-phenylimin)；4-bromo-2-{(E)-[(4-methoxyphenyl)imino]methyl}phenol；4-bromo-2-[(4-methoxyphenyl)iminomethyl]phenol
• CAS: 20772-73-0
• 化学式: C₁₄H₁₂BrNO₂
• 分子量: 306.159
• InChiKey: TYBHINZUFBWUMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-salicylidene-4-methoxyaniline 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以65%的产率得到4-bromo-2-(((4-methoxyphenyl)amino)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
• 作为产物：
  描述：

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

  Phototropic and Thermotropic Anils from 5-Bromosalicylaldehyde

  摘要：

  DOI：

  10.1021/ja01329a049

文献信息

• Asymmetric Synthesis of cis-4-Aminobenzopyran Derivatives Catalyzed by N,N′-Dioxide-Sc(OTf)3 Complexes
  作者：Yulong Zhang、Shunxi Dong、Xiaohua Liu、Mingsheng Xie、Yin Zhu、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.201102058

  日期：2011.12.2

  The reactions of salicylaldimines with electron‐rich alkenes (2,3‐dihydro‐2H‐furan and 3,4‐dihydro‐2H‐pyran) catalyzed by N,N′‐dioxide–Sc(OTf)3 complexes were investigated. The methodology was successfully applied to the asymmetric synthesis of cis‐4‐aminobenzopyran derivatives. Excellent yields, diastereo‐ and enantioselectivities were observed for a broad range of substrates under mild conditions

  研究了水杨醛亚胺与富含电子的烯烃（2,3-二氢-2 H-呋喃和3,4-二氢-2 H-吡喃）在N，N'-二氧化物-Sc（OTf）3配合物催化下的反应。该方法已成功地用于不对称合成顺-4-氨基苯并吡喃衍生物。在温和条件下，对多种底物均观察到优异的收率，非对映和对映选择性（参见方案）。
• Catalytic Asymmetric Mannich-Ketalization Reaction: Highly Enantioselective Synthesis of Aminobenzopyrans
  作者：Magnus Rueping、Ming-Yuan Lin

  DOI：10.1002/chem.201000203

  日期：2010.4.12

  Domino catalysis: We have developed the first enantioselective domino Mannich–ketalization reaction of o‐hydroxy benzaldimines with electron‐rich alkenes (see scheme). The new reaction sequence provides an easy and direct access to optically pure 4‐aminobenzopyrans in good yields and with excellent enantiomeric ratios (up to e.r. 98:2).

  多米诺催化：我们已经开发的第一对映选择性多米诺曼尼期反应缩酮Ø丰富的电子羟基benzaldimines与烯烃（见计划）。新的反应顺序可轻松直接获得光学纯的4-氨基苯并吡喃，并具有良好的收率和出色的对映体比率（可达er 98：2）。
• 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。
• 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
• Antihyperglycemic, α-glucosidase inhibitory and DPPH free radical scavenging activity of 5-bromosalicylaldehyde and schiff bases
  作者：Sristicheta Misra、Krishna Bihari Pandeya、Ashok Kumar Tiwari、Amtul Zehra Ali、Thimmapatruni Saradamani、Sachin Bharat Agawane、Kuncha Madhusudana

  DOI：10.1007/s00044-010-9377-3

  日期：2011.12

  alpha-Glucosidase inhibition and DPPH free radical scavenging by 5-bromosalicylaldehyde and some Schiff bases have been measured. 5-Bromosalicylaldehyde shows lowest IC50 value (8.80 mu M) for alpha-glucosidase inhibition and also shows good results in in vivo experiments for antihyperglycemic potential.