4-bromo-2-(((4-methoxyphenyl)amino)methyl)phenol | 763132-62-3

• 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: 4-bromo-2-(((4-methoxyphenyl)amino)methyl)phenol
• 英文别名: N-p-methoxyphenyl-N-2-hydroxy-5-bromobenzylamine；4-bromo-2-((4-methoxyphenylamino)methyl)-phenol；4-Bromo-2-[(4-methoxyanilino)methyl]phenol
• CAS: 763132-62-3
• 化学式: C₁₄H₁₄BrNO₂
• 分子量: 308.175
• InChiKey: YGTRENLQWRENHX-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  443.5±40.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  劳森试剂 、 4-bromo-2-(((4-methoxyphenyl)amino)methyl)phenol 以 甲苯 为溶剂， 以38.3%的产率得到6-bromo-2,3-bis(4-methoxyphenyl)-2-sulfanylidene-4H-1,3,2lambda5-benzoxazaphosphinine
  参考文献：
  名称：

  使用劳森试剂合成新的苯并恶氮膦/苯并恶氮磷/二氮杂磷杂膦-2-硫化物

  摘要：

  摘要 通过劳森试剂 (LR) 与 4-溴-2-[(苯氨基) 甲基]苯酚 (1a)、4-溴-2-[(4 -氯/溴/甲氧基/甲基苯基-氨基）甲基]苯酚（1b-e），4-溴-2-[（苄基氨基）甲基]苯酚（1f），2-氨基-4-氯苯酚（2a）/2-氨基-4-甲基苯酚 (2b​​), 1,8-二氨基萘 (3) 分别在无水甲苯中。产物 4a-f、5a-b 和 6 通过 IR、1H、13C、31P NMR 和质谱进行表征。

  DOI：

  10.1080/00397910701649148
• 作为产物：
  描述：

  4-溴苯酚 在 sodium tetrahydroborate 、 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 4-bromo-2-(((4-methoxyphenyl)amino)methyl)phenol
  参考文献：
  名称：

  Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines

  摘要：

  Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.064

文献信息

• Synthesis, Characterization, Stability and Cytotoxic Evaluation of Novel Titanium(IV) Complexes of 8-Hydroxyquinoline and 2-Hydroxy-N-phenylbenzylamine Derivatives
  作者：Blassan Samuel、Madhvesh Pathak

  DOI：10.14233/ajchem.2020.22505

  日期：2020.2.10

  A new class of moisture stable heteroleptic titanium(IV) complexes, synthesized from 8-hydroxyquinoline of the type [(Q)2Ti(2-O-5-X-C6H3CH2NC6H4R] (3a-j), was prepared by reacting the antecedent molecule [(Q2)Ti(OiPr)2] (2) with various 2-hydroxy-N-phenyl-benzylamine analogues in 1:1 molar ratios in dry toluene (where, HQ = 8-hydroxyquinoline; iPr = isopropyl; R = H, 4-CH3, 4-OCH3, 2-Cl, 4-Cl, 2-Br, 4-Br; X= H, Br). Moisture sensitive study disclosed that these new metal complexes were unreacted for 72 h. Mass spectral data were employed for proving the mono-nuclearity of the new derivatives. Thermal decomposition pattern of the new derivatives was explained by thermogravimetric analyses. Elemental analyses data are in concordance with their expected values. The hexa-coordinated way of titanium-ligand linkage is further proved through NMR, FTIR, and UV-visible spectral studies. The cytotoxic efficiency of new complexes was tested against MDA-MB-231 human breast carcinoma cell line. Complex 3a exhibited the highest cytotoxic potential of 0.039 μM in comparison to all its analogues of this series by employing cisplatin as the standard

  一种新型的具有湿度稳定性的杂环钛（IV）配合物类别，由8-羟基喹啉[(Q)2Ti（2-O-5-X-C6H3CH2NC6H4R]（3a-j）合成，通过在干燥甲苯中以1:1摩尔比反应前体分子[(Q2)Ti（OiPr）2]（2）与各种2-羟基-N-苯基苄胺类似物（其中，HQ = 8-羟基喹啉; iPr = 异丙基; R = H，4-CH3，4-OCH3，2-Cl，4-Cl，2-Br，4-Br; X = H，Br）。湿度敏感性研究表明，这些新金属配合物在72小时内未反应。质谱数据用于证明新衍生物的单核性。通过热重分析解释了新衍生物的热分解模式。元素分析数据与预期值一致。通过NMR，FTIR和UV-Visible光谱研究进一步证明了钛-配体键合的六配位方式。测试了新配合物对MDA-MB-231人乳腺癌细胞系的细胞毒性效率。与所有同系列的类似物相比，3a复合物表现出最高的细胞毒性潜力（0.039μM），以顺铂为标准。
• 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.
• Oxidative Dehydrogenation of Cu(II) Complexes with N-Aryl-N-2-hydroxybenzyl- and N-Aryl-N-2-hydroxynaphthylmethyleneamine Derivatives
  作者：V. G. Usatyuk、A. A. Medzhidov、A. Aydin、B. Yalchin、R. A. Manafova

  DOI：10.1023/b:ruco.0000040725.54156.bb

  日期：2004.9

  The reactions of Cu2+ Cu2+, and Ni2+ ions with N-phenyl-N-2-hydroxybenzyl- and N-phenyl-N-2-hydroxynaphthylmethyleneamine derivatives (HLn, n = 1-8) produced from the derivatives of aniline and aromatic o-hydroxyaldehydes are studied. Among the ions studied, only Cu2+ forms stable complexes Cu(L-n)2 . 2H(2)O. The structures of the synthesized compounds are studied by IR, UV, and EPR spectroscopies and differential thermal analysis. The magnetic moments of the Cu(L-n)(2) . 2H(2)O complexes are very small and range within 0.43-1.19 mu(B), depending on the ligand structure, which indicates a strong antiferromagnetic interaction between the Cu2+ ions. The temperature dependence of the magnetic susceptibility measured for the Cu(L-3)(2) . 2H(2)O complex (where HL3 is N-4-methoxyphenyl-N-2-hydroxybenzylamine) is closest to the theoretical curve calculated for the binuclear Cu(II) complexes connected by the intermolecular exchange interaction. The Cu(II) complexes with HLn are shown to undergo oxidative dehydrogenation to form the corresponding metal salicylaldiminates. This reaction can occur on heating in the absence of oxygen and is accompanied by the Cu2+ --> Cu+ transition.
• Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines
  作者：Hany F. Anwar、Lars Skattebøl、Trond Vidar Hansen

  DOI：10.1016/j.tet.2007.07.064

  日期：2007.10

  Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of New Benzoxazaphosphinine/Benzoxazaphosphole/Diazaphosphaphenalene‐2‐sulfides using Lawesson's Reagent
  作者：G. Syam Prasad、B. Hari Babu、C. Devendranath Reddy、C. Naga Raju、C. Suresh Reddy

  DOI：10.1080/00397910701649148

  日期：2007.12.1

  Abstract Synthesis of new benzoxazaphosphinine/benzoxazaphosphole/diazaphosphaphenalene 2‐sulfides were accomplished by the reaction of Lawesson's reagent (LR) with 4‐bromo‐2‐[(phenylamino) methyl]phenol (1a), 4‐bromo‐2‐[(4‐chloro/bromo/methoxy/methylphenyl‐amino)methyl]phenol (1b–e), 4‐bromo‐2‐[(benzylamino)methyl]phenol (1f), 2‐amino‐4‐chlorophenol (2a)/2‐amino‐4‐methylphenol (2b), 1,8‐diaminonaphthalene

  摘要 通过劳森试剂 (LR) 与 4-溴-2-[(苯氨基) 甲基]苯酚 (1a)、4-溴-2-[(4 -氯/溴/甲氧基/甲基苯基-氨基）甲基]苯酚（1b-e），4-溴-2-[（苄基氨基）甲基]苯酚（1f），2-氨基-4-氯苯酚（2a）/2-氨基-4-甲基苯酚 (2b​​), 1,8-二氨基萘 (3) 分别在无水甲苯中。产物 4a-f、5a-b 和 6 通过 IR、1H、13C、31P NMR 和质谱进行表征。