N,N'-bis[(E)-(4-methylphenyl)methylidene]benzene-1,2-diamine | 868557-64-6

• 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: N,N'-bis[(E)-(4-methylphenyl)methylidene]benzene-1,2-diamine
• 英文别名: 1-(4-methylphenyl)-N-[2-[(4-methylphenyl)methylideneamino]phenyl]methanimine
• CAS: 868557-64-6
• 化学式: C₂₂H₂₀N₂
• 分子量: 312.414
• InChiKey: KCXUUUSKZSOZKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-bis[(E)-(4-methylphenyl)methylidene]benzene-1,2-diamine 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以95%的产率得到1-(4-methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole
  参考文献：
  名称：

  Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

  摘要：

  An efficient synthetic method for the highly selective synthesis of pharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromatic aldehydes catalyzed byp-toluenesulfonic acid through grinding under solvent-free condition is described. The reaction requires the catalyst only during the conversion of intermediateN,N '-dibenzylidene-o-phenylenediamine into the desired product. The products were obtained within a short time with good yields by using only a mortar and pestle, which makes the proposed method convenient and cost-effective.

  DOI：

  10.1134/s1070428020090201
• 作为产物：
  描述：

  对甲基苯甲醛 、 邻苯二胺 以 四氢呋喃 为溶剂， 生成 N,N'-bis[(E)-(4-methylphenyl)methylidene]benzene-1,2-diamine
  参考文献：
  名称：

  N，N-二苄基-环己烷-1,2-二胺衍生物的合成，抗菌活性和构效关系研究

  摘要：

  我们在本文中报道了一系列N，N-二苄基-环己烷-1,2-二胺衍生物的合成和抗菌活性。为了研究取代的二苄基-环己烷-1，2-二胺衍生物的结构-活性关系，合成了44种结构多样的化合物，并针对革兰氏阳性和革兰氏阴性细菌菌株进行了测试。其中，化合物17-20，26，37，38被发现是比MIC值范围0.0005-0.032微克/毫升四环素和在哺乳动物红细胞不溶血高达1024微克/毫升，观察到更活跃。一些化合物还显示出对白念珠菌非常有希望的抗真菌活性，光滑念珠菌和Geotrichum念珠菌。

  DOI：

  10.1016/j.ejmech.2010.11.027

文献信息

• Eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using alumina-sulfuric acid as a heterogeneous reusable catalyst
  作者：Amit Pramanik、Rimi Roy、Sagar Khan、Avishek Ghatak、Sanjay Bhar

  DOI：10.1016/j.tetlet.2014.01.125

  日期：2014.3

  A cost-effective and eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles has been developed through the condensation of different aldehydes with o-phenylenediamine using alumina-sulfuric acid as a recyclable heterogeneous solid acid catalyst. Morphological properties of the catalyst have been investigated. Effect of different solvents and comparison of alumina-sulfuric acid with different acid catalysts have also been studied. A plausible mechanistic pathway has been proposed on the basis of the isotope labelling experiments where catalytic behaviour of alumina-sulfuric acid has been explained. (C) 2014 Elsevier Ltd. All rights reserved.