3,3’-([1,1’-biphenyl]-4-yl-methylene)bis(1H-indole)

• 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: 3,3’-([1,1’-biphenyl]-4-yl-methylene)bis(1H-indole)
• 英文别名: 3,3'-([1,1'-biphenyl]-4-ylmethylene)bis(1H-indole)；3-[1H-indol-3-yl-(4-phenylphenyl)methyl]-1H-indole
• 化学式: C₂₉H₂₂N₂
• 分子量: 398.507
• InChiKey: GJLOSJJIJKPDOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,3’-([1,1’-biphenyl]-4-yl-methylene)bis(1H-indole) 、 甲烷磺酸 在 重铬酸吡啶 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到bis(1H-indol-3-yl)((1,1‘-biphenyl)-4-yl)methylium methanesulfonate
  参考文献：
  名称：

  Optimization of novel oxidative DIMs as Nur77 modulators of the Nur77-Bcl-2 apoptotic pathway

  摘要：

  DOI：

  10.1016/j.ejmech.2020.113020
• 作为产物：
  描述：

  吲哚 、 4-氨基乙基联苯 在 copper(l) iodide 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 乙腈 为溶剂， 以80%的产率得到3,3’-([1,1’-biphenyl]-4-yl-methylene)bis(1H-indole)
  参考文献：
  名称：

  TEMPO/CuI synergetic catalyzed oxidative cross-coupling of indoles with benzylamines: Synthesis of bis(indolyl)phenylmethanes

  摘要：

  TEMPO/CuI was found to be an effective catalyst for the cross-coupling of indoles with benzylic amines affording the corresponding bis(indolyl)phenylmethanes under air atmosphere at room temperature in good to excellent yields. The efficiency, easy workup, simplicity, and chemoselectivity of this protocol provide a green and low-cost procedure for the synthesis of these compounds.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1459722

文献信息

• Synthesis of 3‐substituted indoles promoted by pulverization‐activation method catalyzed by Bi(NO ₃ ) ₃ ·5H ₂ O
  作者：Mohammad M. Khodaei、Parvin Ghanbary、Iraj Mohammadpoor‐Baltork、Hamid R. Memarian、Ahmad R. Khosropour、Kobra Nikoofar

  DOI：10.1002/jhet.5570450213

  日期：2008.3

  A new, facile, efficient, “green” and chemoselective procedure for the synthesis of indole derivatives has been developed with pulverization-activation method catalyzed by Bi(NO3)3·5H2O (PAMC- Bi(NO3)3·5H2O) through grinding of indoles with aldehydes or Michael acceptors in the presence of catalytic amounts of Bi(NO3)3·5H2O under solvent-free conditions.

  利用Bi（NO 3）3 ·5H 2 O（PAMC- Bi（NO 3）3 ·5H 2 O）通过在催化量的铋（存在NO与醛或迈克尔受体的吲哚的磨削3）3 ·5H 2 ö无溶剂下的条件。
• Development of an imidazole salt catalytic system for the preparation of bis(indolyl)methanes and bis(naphthyl)methane
  作者：Xu Wang、Courtney C. Aldrich

  DOI：10.1371/journal.pone.0216008

  日期：——

  Imidazolium salts are shown to catalyze the rapid room temperature reaction of indoles or naphthol with aldehydes to provide bis(indolyl)methanes or bis(naphthol)methane in excellent yields and the reaction proceeds optimally in dichloromethane with no base additives. The reaction exhibits a broad substrate tolerance and occurs through nucleophilic activation of the indoles and naphthols through a

  已显示咪唑鎓盐催化吲哚或萘酚与醛的快速室温反应，从而以优异的收率提供双（吲哚基）甲烷或双（萘酚）甲烷，并且该反应在无碱添加剂的二氯甲烷中最佳进行。该反应表现出广泛的底物耐受性，并且通过阳离子-π相互作用通过吲哚和萘酚的亲核活化而发生。
• Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols
  作者：Avijit Mondal、Rahul Sharma、Bishal Dutta、Debjyoti Pal、Dipankar Srimani

  DOI：10.1021/acs.joc.1c02702

  日期：2022.3.18

  Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates

  在此，我们展示了 Mn 催化的吲哚与醇的选择性 C-3 官能化。开发的催化剂还可以在稍微改进的反应条件下从同一组底物提供双（吲哚基）甲烷。机理研究表明，吲哚的 C-3 官能化是通过借氢途径进行的。为了突出实用性，合成了多种底物，包括九种结构上重要的药物分子。此外，我们还介绍了一种一锅级联策略，用于直接从 2-氨基苯基乙醇和酒精合成 C-3 官能化吲哚。
• Sulfonated Organic Heteropolyacid Salts: Recyclable Green Solid Catalysts for the Highly Efficient and Green Synthesis of Bis(indolyl)methanes in Water
  作者：Seyed M. Vahdat、Samad Khaksar、Saeed Baghery

  DOI：10.2174/157017812800221690

  日期：2012.2.1

  In the present study, we introduce two nonconventional ionic liquids [MIMPS]3PW12O40 (a) and [TEAPS]3PW12O40 (b) as green solid acid catalysts for the efficient synthesis of bis(indolyl)methanes. The reaction of indole with aldehydes or ketones in water afforded the corresponding bis(indolyl)methanes in excellent yields. This reaction has been carried out in the presence of 1 mol% of catalysts at room temperature. The reusability of the catalysts was demonstrated by a six-run test. Additionally, the catalysts pose several advantages including mild reaction conditions, cleaner reactions and shorter reaction times.

  在本研究中，我们引入了两种非常规离子液体[MIMPS]3PW12O40 (a) 和[TEAPS]3PW12O40 (b) 作为绿色固体酸催化剂，用于高效合成双（吲哚基）甲烷。吲哚与醛或酮在水中的反应以优异的产率得到相应的双（吲哚基）甲烷。该反应在室温下进行，催化剂用量为1 mol%。通过六轮测试证明了催化剂的可重复使用性。此外，这些催化剂还具有温和的反应条件、反应更清洁和反应时间更短等优点。
• Ionic Liquid Tributyl (Carboxymethyl) Phosphonium Bromide as an efficient Catalyst for the Synthesis of bis(indolyl)Methanes under Solvent-Free Conditions
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Toktam Faal-Rastegar

  DOI：10.3184/174751913x13787959859380

  日期：2013.10

  A simple green synthesis of bis (indolyl)methanes involved the reaction of indole with aldehydes in the presence of a phosphonium salt ionic liquid as the catalyst. The simple experimental procedures, short reaction times, high yields of product, non-toxic catalyst and the absence of solvent are the advantages of this method.

  双（吲哚基）甲烷的简单绿色合成涉及在作为催化剂的鏻盐离子液体存在下吲哚与醛的反应。该方法具有实验步骤简单、反应时间短、产物收率高、催化剂无毒、无溶剂等优点。