2-((4-硝基苯基氨基)甲基)苯酚 | 13159-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-((4-硝基苯基氨基)甲基)苯酚
• 英文名称: 2-hydroxybenzyl(p-nitrophenyl)amine
• 英文别名: 2-(((4-nitrophenyl)amino)methyl)phenol；2-(4-nitro-anilinomethyl)-phenol；N-(2-Oxy-benzyl)-4-nitro-anilin；2-[(4-Nitroanilino)methyl]phenol
• CAS: 13159-73-4
• 化学式: C₁₃H₁₂N₂O₃
• mdl: MFCD00024630
• 分子量: 244.25
• InChiKey: XXFBEWGVOTUXHP-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C(Solv: methanol (67-56-1))
• 沸点：
  444.3±30.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  2-((4-硝基苯基氨基)甲基)苯酚 在 tetraphosphorus decasulfide 、 potassium carbonate 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 丙酮 、 苯 为溶剂， 反应 7.0h， 生成 4-(4-nitrophenyl)-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione
  参考文献：
  名称：

  Synthesis and structure–antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones

  摘要：

  The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.

  DOI：

  10.1007/s00044-010-9457-4
• 作为产物：
  描述：

  2-((4-nitrophenylimino)methyl)phenol 在 nickel(II) oxide 、 甲酸铵 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以97%的产率得到2-((4-硝基苯基氨基)甲基)苯酚
  参考文献：
  名称：

  一种使用生物合成的氧化镍纳米粒子还原席夫碱的简单方法

  摘要：

  描述了使用生物合成的氧化镍纳米粒子作为多相催化剂，甲酸铵作为氢供体，将醛亚胺还原为相应的仲胺的创新而简单的方法。这种催化转移加氢方法非常高效，并有助于以极高的收率且没有任何粗糙环境合成胺。

  DOI：

  10.1080/24701556.2020.1783683

文献信息

• Qualitative Analysis of the Stability of the Oxazine Ring of Various Benzoxazine and Pyridooxazine Derivatives with Proton Nuclear Magnetic Resonance Spectroscopy
  作者：Gerard P. Moloney、David J. Craik、Magdy N. Iskander

  DOI：10.1002/jps.2600810721

  日期：1992.7

  3-benzoxazine and 3,4-dihydro-1,3-pyridooxazine derivatives was synthesized, and the hydrolysis of the derivatives was studied with proton nuclear magnetic resonance spectroscopy. The oxazine derivatives underwent various degrees of hydrolysis when H2O was added to dimethyl sulfoxide solutions of the compounds. The rates and extents of decomposition of the oxazine ring systems depended on the electronic effects

  合成了一系列的3,4-二氢-1,3-苯并恶嗪和3,4-二氢-1,3-吡啶并恶嗪衍生物，并利用质子核磁共振波谱研究了这些衍生物的水解。当将H 2 O加入到化合物的二甲基亚砜溶液中时，恶嗪衍生物经历了不同程度的水解。恶嗪环系统分解的速率和程度取决于分子内取代基的电子效应。对恶嗪分解期间产生的质子核磁共振谱以及恶嗪衍生物的稳定性趋势的研究表明在水解机理中形成了中间体。
• Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves
  作者：Rajender S. Varma、Rajender Dahiya

  DOI：10.1016/s0040-4020(98)00326-3

  日期：1998.6

  A solvent-free reductive amination of carbonyl compounds by wet montmorillonite K 10 clay supported sodium borohydride is described; microwave irradiation facilitates the procedure.

  描述了通过湿蒙脱石K 10粘土负载的硼氢化钠对羰基化合物进行无溶剂还原胺化反应。微波辐射使该过程变得容易。
• Screening of simple carbohydrates as a renewable organocatalyst for the efficient construction of 1,3-benzoxazine scaffold
  作者：Ayhan Yıldırım、Yunus Kaya、Mustafa Göker

  DOI：10.1016/j.carres.2021.108458

  日期：2021.12

  performed to study the detailed mechanism of organocatalyst assisted synthesis of the benzoxazine monomers. The results obtained from these calculations showed that the more realistic reaction pathway involves formation of a phenolate based intermediate which loses a water molecule to form benzenaminium ion. Subsequently, this ion provides the formation of the corresponding benzoxazines with good yields

  已经开发了一种通过使用几种受保护和未受保护的碳水化合物分子作为有机催化剂制备 1,3-苯并恶嗪的简便方案，该方案广泛适用于各种曼尼希碱和多聚甲醛之间的缩合反应。该研究表明，果糖比其他碳水化合物具有更高的催化活性，可以作为含金属催化剂的替代品，作为一种绿色可再生有机催化剂，用于高效、快速地构建 1,3-苯并恶嗪骨架。在此背景下，成功合成了 21 种苯并恶嗪化合物，并通过光谱方法和元素分析对这些化合物进行了光谱表征。此外，已经进行了密度泛函理论 (DFT) 计算，以研究有机催化剂辅助合成苯并恶嗪单体的详细机理。从这些计算中获得的结果表明，更现实的反应途径涉及形成基于酚盐的中间体，该中间体失去水分子以形成苯甲胺离子。随后，该离子通过分子内闭环步骤以良好的产率形成相应的苯并恶嗪。
• <i>N</i> ‐alkyl imidazole‐based homonuclear coordination complex as a neutral organocatalyst for the faster and efficient construction of 3,4‐dihydro‐2 <i>H</i> ‐1,3‐oxazine scaffold
  作者：Ayhan Yıldırım、Mustafa Göker

  DOI：10.1002/aoc.6425

  日期：2021.12

  N-hexadecylimidazole ligand was used for the first time as a highly efficient homogeneous neutral organocatalyst for the synthesis of 3,4-dihydro-2H-1,3-benzoxazine monomers. Therefore, N-alkyl or N-aryl substituted, both mono-benzoxazine and bis-benzoxazine, were successfully synthesized (21 examples) via Mannich-type condensation reactions. Effortlessly obtaining the pure product with high yields

  在目前的工作中，包括 Zn (II) 和N-十六烷基咪唑配体的同核配位络合物首次用作合成 3,4-二氢-2 H -1,3-苯并恶嗪单体的高效均相中性有机催化剂. 因此，通过曼尼希型缩合反应成功合成了N-烷基或N-芳基取代的单苯并恶嗪和双苯并恶嗪（21 个实例）。毫不费力地以高收率和短反应时间获得纯产物，使该方法比现有的常见苯并恶嗪合成方法更有用和更有利。
• Structure–activity relationship study of E6 as a novel necroptosis inducer
  作者：Jianfeng Mou、Ann Park、Yu Cai、Junying Yuan、Chengye Yuan

  DOI：10.1016/j.bmcl.2015.04.038

  日期：2015.8

  Necroptosis inducers represent a promising potential treatment for drug-resistant cancer. We herein describe the structure modification of E6, which was identified recently as a potent and selective necroptosis inducer. The studies described herein demonstrate for the first time that functionalized biphenyl derivatives possess necroptosis inducer activity. Furthermore, these studies have led to the identification of two promising compounds (5h and 5j) that can be used for further optimization studies as well as mechanism of action investigations. (C) 2015 Elsevier Ltd. All rights reserved.