N-p'-methoxybenzylidene-o-phenylenediamine | 85972-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-p'-methoxybenzylidene-o-phenylenediamine
• 英文别名: 2-[(4-Methoxyphenyl)methylideneamino]aniline
• CAS: 85972-04-9
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: NXENGMCTTCEJFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-p'-methoxybenzylidene-o-phenylenediamine 在 硼酸 、 甘油 作用下， 以 水 为溶剂， 生成 2-(4-甲氧基苯基)-1H-苯并咪唑
  参考文献：
  名称：

  硼酸和甘油的水介导合成2-取代的苯并咪唑

  摘要：

  已开发出一种非常简单，温和且高效的绿色催化剂，用于在硼酸（5摩尔％）和80℃的存在下于80°C的水中处理取代的邻苯二胺和醛来合成2-取代的苯并咪唑。甘油（0.05 mL）。该方法已在55种底物上标准化，并合成了9种新化合物。

  DOI：

  10.1071/ch08309
• 作为产物：
  描述：

  2,2'-((4-methoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) 、 邻苯二胺 以 异丙醇 为溶剂， 以40%的产率得到N-p'-methoxybenzylidene-o-phenylenediamine
  参考文献：
  名称：

  Investigation of the products of interaction of cyclic diketones with nitrogen-containing 1,4-binucleophiles

  摘要：

  DOI：

  10.1007/s10593-005-0098-3

文献信息

• An Efficient and Environmental Benign Synthesis of 2-benzimidazoles and 2-benzothiazoles Using CeCl₃-NaI as Catalyst
  作者：Xun Zhu、Yunyang Wei

  DOI：10.3184/174751913x13575704209748

  日期：2013.2

  A one-pot condensation of an aldehyde with 1,2-phenylenediamine or 2-aminothiophenol in dimethyl carbonate at 100 °C under O2 in the presence of catalytic amounts of CeCl3–NaI gave an imine intermediate, which cyclised and dehydrogenated to give 2-arylbenzimidazoles or 2-arylbenzothiazoles in good yields.

  醛与 1,2-苯二胺或 2-氨基苯硫酚在碳酸二甲酯中于 100 °C 在 O2 和催化量的 CeCl3-NaI 存在下进行一锅缩合得到亚胺中间体，该中间体环化并脱氢得到 2-芳基苯并咪唑或 2-芳基苯并噻唑收率良好。
• Superoxide Ion Promoted Synthesis of 2-Arylbenzimidazoles from Schiff Bases
  作者：Raghvendra S. Raghuvanshi、Virendra P. Yadav、Vinod K. Singh

  DOI：10.2174/1570178612666151028210206

  日期：2015.12.2

  Background: Benzimidazoles exhibit a wide range of biological activities, including antiparasitic, antiulcer, antihypertensive, antihistaminic, anticancer, antiemetic and antiinflammatory agents. Methods: Tetraethylammonium superoxide has been generated in situ by the phase transfer reaction of potassium superoxide and tetraethylammonium bromide in dry dimethylformamide at room temperature and subsequently allowed to react with a number of Schiff's bases. Results: The Synthesis of 2-arylbenzimidazoles from Schiff bases using in situ generated tetraethylammonium superoxide in dry DMF, at room temperature. Conclusion: The role of in situ generated Et4NO2 as an efficient agent to promote the synthesis of 2-arylbenzimidazole from Schiff base has been demonstrated under mild conditions.

  背景：苯并咪唑具有广泛的生物活性，包括抗寄生虫药、抗溃疡药、抗高血压药、抗组胺药、抗癌药、止吐药和抗炎药。 方法：在室温下，通过超氧化钾和四乙基溴化铵在干燥的二甲基甲酰胺中发生相转移反应，在原位生成四乙基超氧化铵，然后让其与一些希夫碱发生反应。 结果：合成了 2-芳基溴化铵：在室温下，利用原位生成的四乙基铵超氧化物在干燥的 DMF 中从希夫碱合成 2-芳基苯并咪唑。 结论：在温和的条件下，原位生成的 Et4NO2 作为一种高效制剂，促进了从希夫碱合成 2-芳基苯并咪唑的过程。
• Novel Method for the Syntheses of 2-Substituted Benzimidazoles Using Ti(IV) Isopropoxide and Cumene Hydroperoxide
  作者：Freddy H. Havaldar、Ganesh Mule、Bhushan Dabholkar

  DOI：10.1080/00397911.2011.571803

  日期：2011.8

  Abstract Various 2-substituted benzimidazoles were prepared in one pot by condensation of o-phenylenediamine with an appropriate aldehyde in good to excellent yields using a mixture of Ti(IV) isopropoxide and cumene hydroperoxide.

  摘要 使用 Ti(IV) 异丙醇和枯烯氢过氧化物的混合物，通过邻苯二胺与适当的醛缩合反应，在一个锅中制备了各种 2-取代苯并咪唑。
• Modifying the Oxidative Potentials of Imines in a Dye Loaded Capsule for Photocatalytic Cyclization with Hydrogen Evolution
  作者：Yang Yang、Hanning Li、Youpeng Shi、Yuchen Wu、Xu Jing、Chunying Duan

  DOI：10.1002/anie.202319605

  日期：2024.3.11

  Through the confinement effect of the host-dye photocatalytic system to shift the redox potentials of substrate, the isomerization and thermodynamic activation of substrate were achieved, which were followed by a multiphoton excitation enzymatic strategy for the generation of heterocycles by intramolecular C−X hydrogen evolution cross-couplings.

  通过主体-染料光催化系统的限域效应改变底物的氧化还原电位，实现底物的异构化和热力学活化，随后采用多光子激发酶促策略通过分子内C−X析氢生成杂环交叉耦合。
• Ni Nanoparticles: Mild and Efficient Catalyst for the Chemoselective Synthesis of 2-Arylbenzimidazoles, 2-Arylbenzothiazoles, and Azomethines
  作者：Jitender M. Khurana、Sneha、Kanika Vij

  DOI：10.1080/00397911.2011.563404

  日期：2012.9

  A new and efficient method has been developed for the synthesis of biologically significant 2-arylbenzimidazoles, 2-arylbenzothiazoles, and azomethines using recyclable and inexpensive polyvinyl pyrrolidone (PVP)-stabilized Ni nanoparticles in ethylene glycol at room temperature in excellent yields.