2-[[4-[(2-羟基苯基)甲氨基]苯胺基]甲基]苯酚 | 34579-88-9

• 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-[(2-羟基苯基)甲氨基]苯胺基]甲基]苯酚
• 英文名称: N,N'-bis-(2-hydroxybenzyl)benzene-1,4-diamine
• 英文别名: 2-(4-[(2-hydroxybenzyl)amino]phenylaminomethyl)phenol；PDA-HB-r；2,2'-(1,4-phenylene-bis(azanediyl)-bis(methylene))diphenol；2,2'-[1,4-Phenylenebis(azanediylmethylene)]diphenol；2-[[4-[(2-hydroxyphenyl)methylamino]anilino]methyl]phenol
• CAS: 34579-88-9
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: FYFIWSVKNZPSQC-UHFFFAOYSA-N

物化性质

• 沸点：
  547.6±45.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[4-[(2-羟基苯基)甲氨基]苯胺基]甲基]苯酚 在 三氯硫磷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 2-chloro-3-[4-(2-chloro-2-sulfanylidene-4H-1,3,2lambda5-benzoxazaphosphinin-3-yl)phenyl]-2-sulfanylidene-4H-1,3,2lambda5-benzoxazaphosphinine
  参考文献：
  名称：

  3,3'-（1,4-亚苯基）-双[2-烷氧基羰基-烷基）-2-硫代-苯并氧膦的合成，光谱表征和生物测定

  摘要：

  3,3'-（1,4-亚苯基）-双[2-烷氧基羰基-烷基）-2-硫代-苯并氧杂膦]（3a – j）的合成是通过两步过程完成的。它涉及先制备一氯化物中间体（2），然后使其与氨基酸酯在干燥的四氢呋喃-甲苯中，在三乙胺存在下，在回流温度下反应。这些化合物的特征在于IR，1 H，13 C，31 P NMR，并显示出有效的体外抗氧化活性。

  DOI：

  10.1016/j.ejmech.2010.01.019
• 作为产物：
  描述：

  N,N'-bis(2-hydroxybenzylidene)-p-phenylenediamine 在 sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-[[4-[(2-羟基苯基)甲氨基]苯胺基]甲基]苯酚
  参考文献：
  名称：

  Studies on structurally different benzoxazines based on diphenols and diamines: Kinetics of thermal degradation and TG-FTIR studies

  摘要：

  Structurally different bisbenzoxazines (QB, RB, pHBA-pd and mHBA-pd) are synthesized using quinol, resorcinol, p-phenylenediamine and m-phenylenediamine and are thermally cured. The thermal stability of the materials was studied using TGA. The plate like structure resulting from the interlinking of the ladders by intermolecular hydrogen bonding provides thermal stability to poly(pHBA-pd). The kinetics of thermal degradation is followed using Vyazovkin and Friedman methods. The diphenol based polybisbenzoxazines show higher apparent activation energy for thermal degradation (Ea-D) (PQB = 252-330 kJ/mol than the diamine based polybisbenzoxazines (poly(pHBA-pd) = 98-188 kJ/mol). Aromatic amines are found to be released in considerable quantities from the diamine based polybisbenzoxazines whereas phenolics are released from diphenol based polybisbenzoxazines. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.tca.2015.09.006

文献信息

• Facile, one-pot synthesis of aromatic diamine-based benzoxazines and their advantages over diamines as epoxy hardeners
  作者：Sheng Lung Chang、Ching Hsuan Lin

  DOI：10.1002/pola.24013

  日期：2010.6.1

  The resultant benzoxazines were applied as hardeners for cresol novolac epoxy (CNE). The processing window, the latent curing characteristic, and the miscibility of benzoxazine/CNE systems were discussed. Compared with diamines (1 and 3), (1 and 3)‐based benzoxazines show latent curing characteristic as epoxy hardeners, and wide processing windows can be obtained. Compared with diamine (2) which is

  通过1,4-苯二胺（1），4,4'-二氨基二苯醚（2）和4,4'-二氨基二苯甲烷（3）通过简便，清洁的一锅法成功制备了三种基于芳族二胺的苯并恶嗪）， 分别。通过NMR光谱和单晶衍射图证实了它们的结构。讨论了二胺的反应性对所得苯并恶嗪纯度的影响。将所得苯并恶嗪用作甲酚酚醛清漆环氧树脂（CNE）的固化剂。讨论了苯并恶嗪/ CNE体系的加工窗口，潜在的固化特性和互溶性。与二胺（1和3）相比，（1和3）-基苯并恶嗪具有作为环氧固化剂的潜在固化特性，并且可以获得宽广的加工窗口。与在熔融状态下与CNE不混溶的二胺（2）相比，基于（2）的苯并恶嗪与CNE具有良好的混溶性。动态力学分析表明，苯并恶嗪/ CNE热固性材料的T g s高达242–243°C。热重分析表明所得热固性塑料具有出色的热稳定性。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem
• <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。
• Manikannan, Ramaiyan; Muthusubramanian, Shanmugam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 8, p. 1083 - 1087
  作者：Manikannan, Ramaiyan、Muthusubramanian, Shanmugam

  DOI：——

  日期：——
• <i>N,N</i>‘-Bisbenzylidenebenzene-1,4-diamines and <i>N,N</i>‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors
  作者：Päivi H. Kiviranta、Jukka Leppänen、Sergiy Kyrylenko、Heikki S. Salo、Maija Lahtela-Kakkonen、Anu J. Tervo、Carsten Wittekindt、Tiina Suuronen、Erkki Kuusisto、Tomi Järvinen、Antero Salminen、Antti Poso、Erik A. A. Wallén

  DOI：10.1021/jm060566j

  日期：2006.12.1

  A series of N,N'-bisbenzylidenebenzene-1,4-diamine and N,N'-bisbenzylidenenaphthalene-1,4-diamine derivatives were synthesized as inhibitors for human sirtuin type 2 (SIRT2). The design of the new compounds was based on two earlier reported hits from molecular modeling and virtual screening. The most potent compound was N,N'-bis(2-hydroxybenzylidene)benzene-1,4-diamine, which was equipotent with the most potent hit compound and well-known SIRT2 inhibitor sirtinol.
• Sustainable synthetic approaches using [C16Im][Oxa] as a flexible organocatalyst and DFT studies toward 3,4-dihydropyrimidinones and benzoxazines
  作者：Ayhan Yıldırım、Yunus Kaya

  DOI：10.1007/s00706-016-1894-4

  日期：2017.6

  Easily accessible 1-hexadecyl-1H-imidazol-3-ium oxalate is highly efficient Bronsted type acidic catalyst for the selected multicomponent one-pot reactions. The short reaction times, easy workup procedures, and green metal-free conditions for the reactions make the protocols more advantageous. Further reactions proceeded smoothly in good to excellent yields with high purity. To investigate mechanism of the multicomponent reactions, DFT calculations were performed.