3,3'-(p-tolylmethylene)bis(5-bromo-1H-indole) | 1189117-61-0

• 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(5-bromo-1H-indole)
• 英文别名: 5-bromo-3-[(5-bromo-1H-indol-3-yl)-(4-methylphenyl)methyl]-1H-indole
• CAS: 1189117-61-0
• 化学式: C₂₄H₁₈Br₂N₂
• 分子量: 494.228
• InChiKey: UAFKYLNETRPHGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  5-溴吲哚 、 对甲基苯甲醛 在 deep eutectic mixture of polyvinylpyrrolidone hydrochloride and ZnCl₂ 作用下， 以 乙醇 为溶剂， 以77 %的产率得到3,3'-(p-tolylmethylene)bis(5-bromo-1H-indole)
  参考文献：
  名称：

  基于 PVP 的低共熔溶剂聚合物：用于合成 α-氨基膦酸酯和双吲哚的可持续 Brønsted-Lewis 酸性催化剂

  摘要：

  聚合物低共熔溶剂 (PDES) 的出现，增强了低共熔溶剂 (DES) 作为可持续材料类别的功能。考虑到PDES对深度共晶单体原位聚合的常见合成限制，本文中，我们采用线性聚乙烯吡咯烷酮（PVP）来开发一种易于制备、原子经济、成本效益高且环境友好的布朗斯台德-通过ZnCl 2和季铵化过程生成路易斯酸性PDES。通过 SEM、EDS、元素图、FT-IR 和 TGA 技术对制备的 PDES 进行了表征。该方法通过改变 ZnCl 2的摩尔比来实现 PDES 的物理化学调节为 PVP 单体重复单元。PDES 被用作非均相催化剂，通过醛、胺和三（烷基/芳基）亚磷酸酯的多组分反应，除了碳之外，还可以合成仲和叔 α-氨基膦酸酯（AP），从而促进具有生物学意义的支架的绿色方法。 –从醛和吲哚基化合物合成双（吲哚基）甲烷（BIM）的碳键形成反应。事实证明，PDES 是这些转变的高效催化剂，为广泛的 AP 和 BIM

  DOI：

  10.1016/j.molliq.2023.122677

文献信息

• Two novel binuclear sulfonic-functionalized ionic liquids: Influence of anion and carbon-spacer on catalytic efficiency for one-pot synthesis of bis(indolyl)methanes
  作者：Nader Ghaffari Khaligh、Taraneh Mihankhah、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1016/j.molliq.2018.03.044

  日期：2018.6

  from pyrazinium, piperazinium, benzimidazolium, imidazolium mono- or di-cation containing chloride and hydrogen sulfate as counter anion under optimized conditions. It was proved that the new ionic liquids containing two sulfonic imidazole moieties with four-carbon spacer as well as hydrogen sulfate as acidic counter anion were superior to the previously reported ionic liquids.

  合成了两种新的具有四碳间隔基的双核磺酸官能化离子液体，并通过FTIR，MS，1 H和13对其结构进行了表征1 H NMR; 然后确定特定任务的新型离子液体水溶液的一些物理性质和pH值。研究了它们在温和条件下的双溶剂催化活性，以合成双（吲哚基）甲烷。在优化的条件下，将这些离子液体的催化活性与衍生自吡嗪鎓，哌嗪鎓，苯并咪唑鎓，咪唑鎓单或二阳离子的氯化物和硫酸氢盐作为抗衡阴离子的某些离子液体进行了比较。事实证明，含有两个带有四个碳间隔基的磺酸咪唑部分以及硫酸氢盐作为酸性抗衡阴离子的新型离子液体优于以前报道的离子液体。
• Palladium(II) in electrophilic activation of aldehydes and enones: efficient C-3 functionalization of indoles
  作者：Swapna Sarita Mohapatra、Priyabrata Mukhi、Anuradha Mohanty、Satyanarayan Pal、Aditya Omprakash Sahoo、Debjit Das、Sujit Roy

  DOI：10.1016/j.tetlet.2015.08.080

  日期：2015.10

  The regioselective C-3 alkylation of indoles with aldehydes and enones as electrophiles is catalyzed by a d8 late transition metal complex PdCl2(MeCN)2 at room temperature in the presence of air/moisture and in the absence of any additional acid/base, additive, or ligand. The active catalyst in this alkylation is an organometallic intermediate C1 which is formed from the reaction of indole with the

  在室温下，在空气/水分存在且没有任何其他酸/碱的情况下，ad 8过渡金属络合物PdCl 2（MeCN）2催化吲哚与醛和烯酮作为亲电子体的区域选择性C-3烷基化反应，添加剂或配体。在该烷基化反应中的活性催化剂是有机金属中间体C1，它是由吲哚与钯（II）预催化剂反应形成的。C1及其类似物与吲哚和代孕化合物的晶体学表征和反应性正在进行中。
• Synthesis of bis(indolyl)methanes using ammonium niobium oxalate (ANO) as an efficient and recyclable catalyst
  作者：Samuel R. Mendes、Samuel Thurow、Filipe Penteado、Maitê S. da Silva、Rogério A. Gariani、Gelson Perin、Eder J. Lenardão

  DOI：10.1039/c5gc00932d

  日期：——

  Bis(indolyl)methanes were efficiently synthesized using ammonium niobium oxalate (ANO) as the catalyst and water or glycerol as the solvent.

  双吲哚基甲烷通过使用草酸铌铵（ANO）作为催化剂，水或甘油作为溶剂，高效合成。
• Novel 3,3′-diindolylmethane derivatives: Synthesis and cytotoxicity, structural characterization in solid state
  作者：Dorota Maciejewska、Magdalena Rasztawicka、Irena Wolska、Elżbieta Anuszewska、Beata Gruber

  DOI：10.1016/j.ejmech.2009.05.011

  日期：2009.10

  A series of 3,3'-dindolylmethane derivatives have been synthesized and their structures were characterized in solid state by C-13 CP/MAS NMR and two of them by X-ray diffraction measurements. They exhibited well expressed cytotoxicity against human melanoma cell lines. Derivatives bearing fluoro, bromo, iodo, and nitro substituents in indole or benzene rings caused 50% inhibition of the viability of ME18 and ME18/R cell lines at concentration ranging 9.7-17.3 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Tetramethyl guanidinium chlorosulfonate as a highly efficient and recyclable organocatalyst for the preparation of bis(indolyl)methane derivatives
  作者：Reddi Mohan Naidu Kalla、Johnson V. John、Huiju Park、Il Kim

  DOI：10.1016/j.catcom.2014.08.003

  日期：2014.12

  The synthesis and characterization of a novel superbase ionic liquid, tetramethylguanidinium chlorosulfonate, are described. The guanidine ionic liquid (GIL) was characterized by FT-IR and NMR spectroscopies, and wide-angle X-ray scattering techniques, as well as thermogravimetric analysis. The GIL functions as an effective, environmentally benign, and recyclable catalyst for the synthesis of various bis(indolyl)methanes in outstanding yields (90-96%), within short reaction times; further, no chromatographic purification step for the product is required. (C) 2014 Elsevier B.V. All rights reserved.