3,3'-(p-tolylmethylene)bis(2-methyl-1H-indole) | 618404-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3'-(p-tolylmethylene)bis(2-methyl-1H-indole)
• 英文别名: 2-methyl-3-((2-methyl-1H-indol-3-yl)-(4-methylphenyl)methyl)-1H-indole；2-methyl-3-((2-methyl-1H-indol-3-yl)(p-tolyl)methyl)-1H-indole；3,3′-(p-tolylmethylene)bis(2-methyl-1H-indole)；bis-(2-methyl-indol-3-yl)-p-tolyl-methane；Bis-(2-methyl-indol-3-yl)-p-tolyl-methan；3,3'-(4-Methylbenzylidene)bis(2-methyl-1H-indole)；2-methyl-3-[(2-methyl-1H-indol-3-yl)-(4-methylphenyl)methyl]-1H-indole
• CAS: 618404-33-4
• 化学式: C₂₆H₂₄N₂
• 分子量: 364.49
• InChiKey: LMFLBIAFVNWCBY-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  586.2±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 对甲基苯甲醛 以 甲醇 为溶剂， 反应 3.5h， 以70%的产率得到3,3'-(p-tolylmethylene)bis(2-methyl-1H-indole)
  参考文献：
  名称：

  室温下质子溶剂中高效清洁合成双（吲哚基）甲烷

  摘要：

  吲哚与各种醛的亲电取代反应在质子溶剂中于室温下在不存在任何其他催化剂的条件下进行，以优异的收率得到双（吲哚基）-甲烷。

  DOI：

  10.1016/j.tetlet.2005.12.093

文献信息

• Synthesis and characterization of a tetracationic acidic organic salt and its application in the synthesis of bis(indolyl)methanes and protection of carbonyl compounds
  作者：Azim Ziyaei Halimehjani、Seyyed Emad Hooshmand、Elham Vali Shamiri

  DOI：10.1039/c5ra01422k

  日期：——

  A new tetracationic acidic organic salt (TCAOS) based on DABCO was prepared, characterized and applied as an eco-friendly, powerful and reusable catalyst for the synthesis of bis(indolyl)methanes from indoles and carbonyl compounds in water with high turnover frequency (TOF). Also, this catalyst was successfully applied for acetalization of carbonyl compounds with diols under solvent-free conditions

  制备了一种新的基于DABCO的四阳离子酸性有机盐（TCAOS），并表征为一种环保，功能强大且可重复使用的催化剂，用于在水中以高周转频率（TOF）从吲哚和羰基化合物合成双（吲哚基）甲烷。 ）。同样，该催化剂成功地用于无溶剂条件下用二醇对羰基化合物的缩醛化反应。
• Uncatalyzed Michael addition of indoles: synthesis of some novel 3-alkylated indoles via a three-component reaction in solvent-free conditions
  作者：Mohit L. Deb、Pulak J. Bhuyan

  DOI：10.1016/j.tetlet.2007.01.105

  日期：2007.3

  Synthesis of some novel 3-alkylated indoles via an uncatalyzed Michael addition of indoles using three components in one-pot solvent-free conditions is reported. The mechanism was established by performing the reaction in two steps. The reaction was also studied in different solvents and an important solvent effect was noticed.

  据报道，在一锅无溶剂的条件下，使用三种组分通过吲哚的未催化迈克尔加成反应合成了一些新型的3-烷基化的吲哚。通过两步进行反应来建立机理。还研究了在不同溶剂中的反应，并注意到重要的溶剂作用。
• Preparation of choline sulfate ionic liquid supported on porous graphitic carbon nitride nanosheets by simple surface modification for enhanced catalytic properties
  作者：Najmedin Azizi、Mahtab Edrisi

  DOI：10.1016/j.molliq.2019.112263

  日期：2020.2

  property of g-C3N4 along with the recyclability of the ionic liquid. g-C3N4@SO3Ch (IL/g-C3N4) offers an effective, reusable, inexpensive, environmentally friendly and low-cost catalyst for the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones, 2,3-dihydroquinazolin-4 (1H)-ones and bisindolylmethanes in good to excellent yields. The prepared catalyst synthesized compounds were well characterized by different

  在过去的几十年中，由于应用范围的多样性，负载型离子液体（SILs）引起了越来越多的关注和积极的研究，然而关于ILs的报道仍在迅速增加。这项工作报告了一种迷人的且高度稳定的多孔石墨碳氮化碳（gC 3 N 4）纳米片上负载的胆碱硫酸盐离子液体，它是通常需要有害有机溶剂和剧毒酸的有机合成中廉价且环保的可重复使用的离子催化剂。GC 3 Ñ 4 @SO 3章的制备是通过混合磺酸官能化的石墨碳纳米片氮化（GC 3 Ñ 4 @SO 3H）用氢氧化胆碱或通过新颖的方法。硫酸胆碱的引入可以显着增大具有丰富反应位点的比表面积，并抑制薄片的复合。这项工作为改善gC 3 N 4的化学性质以及离子液体的可回收性提供了一种新途径。gC 3 N 4 @SO 3通道（IL / gC 3 N 4）为合成3,4-二氢嘧啶2（1H）-酮，2,3-二氢喹唑啉4（1H）-酮和二吲哚基甲烷提供了有效，可重复使用，廉价，环保且低成本的
• Catalyst-free visible-light-induced condensation to synthesize bis(indolyl)methanes and biological activity evaluation of them as potent human carboxylesterase 2 inhibitors
  作者：Yi-Shu Zhao、Hong-Li Ruan、Xiu-Yang Wang、Chen Chen、Pei-Fang Song、Cheng-Wei Lü、Li-Wei Zou

  DOI：10.1039/c9ra08593a

  日期：——

  A mild strategy for visible-light-induced synthesis of bis(indolyl)methanes was developed using aromatic aldehydes and indole as substrates. This reaction could be performed at room temperature under catalyst- and additive-free conditions to synthesize a series of bis(indolyl)methanes in good to excellent yields. In addition, all synthesized bis(indolyl)methanes together with β-substituted indole derivatives

  使用芳香醛和吲哚作为底物，开发了一种用于可见光诱导合成双（吲哚基）甲烷的温和策略。该反应可以在室温下在无催化剂和无添加剂的条件下进行，以良好的收率合成一系列双（吲哚基）甲烷。此外，所有合成的双（吲哚基）甲烷与根据我们之前的工作合成的 β-取代的吲哚衍生物一起，评估了它们对人羧酸酯酶（CES1 和 CES2）的抑制作用。所有被测化合物的一级构效关系分析表明，β-取代吲哚在 β 位点被另一个吲哚基修饰导致对 CES2 的抑制作用显着增强，双吲哚基结构对于 CES2 抑制是必不可少的。
• A green method for the synthesis of bis-indolylmethanes and 3,3′-indolyloxindole derivatives using cellulose sulfuric acid under solvent-free conditions
  作者：Heshmatollah Alinezhad、Asefeh Hagh Haghighi、Fatemeh Salehian

  DOI：10.1016/j.cclet.2009.09.001

  日期：2010.2

  ethanes, bis-1-methylindolylmethanes and 3,3′-diindolyloxindole derivatives from the reaction of indoles with various aldehydes and ketones in the presence of cellulose sulfuric acid under solvent-free conditions is reported. The significant features of this procedure are high yields of the products, mild reaction, solvent-free condition and non-toxicity of the catalyst.

  摘要在纤维素硫酸存在下，吲哚与各种醛和酮反应制得高效的绿色方案，用于制备双吲哚甲烷，双-2-甲基吲哚甲烷，双-1-甲基吲哚甲烷和3,3'-二吲哚氧基吲哚衍生物。据报道在无溶剂条件下。该方法的显着特征是产物的产率高，反应温和，无溶剂条件和催化剂无毒。