3,3'-[[3-(phenyloxy)phenyl]methyl]bis[1H-indol] | 294636-38-7

• 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'-[[3-(phenyloxy)phenyl]methyl]bis[1H-indol]
• 英文别名: 3,3’-((3-phenoxyphenyl)methylene)bis(1H-indole)
• CAS: 294636-38-7
• 化学式: C₂₉H₂₂N₂O
• 分子量: 414.506
• InChiKey: BHVOOBBVTLUINR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  40.81
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  吲哚 、 间苯氧基苯甲醛 在 [3-(1-methylimidazolium-3-yl)propane-1-sulfonate]3PW₁₂O₄₀ 作用下， 以 水 为溶剂， 反应 0.15h， 以93%的产率得到3,3'-[[3-(phenyloxy)phenyl]methyl]bis[1H-indol]
  参考文献：
  名称：

  Sulfonated Organic Heteropolyacid Salts: Recyclable Green Solid Catalysts for the Highly Efficient and Green Synthesis of Bis(indolyl)methanes in Water

  摘要：

  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。

  DOI：

  10.2174/157017812800221690

文献信息

• 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。
• 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。
• Room temperature ionic liquid choline chloride–oxalic acid: A versatile catalyst for acid-catalyzed transformation in organic reactions
  作者：Urmiladevi Narad Yadav、Ganapati Subray Shankarling

  DOI：10.1016/j.molliq.2013.11.036

  日期：2014.3

  An efficient and facile synthesis of hydrazones, bis(indolyl)methanes and bis(4-hydroxycoumarin)methanes is facilitated by room temperature ionic liquid choline chloride–oxalic acid (ChCl:Ox). ChCl:Ox (10 mol%) efficiently catalyzes condensation of aldehydes with phenylhydrazine giving corresponding hydrazones in high yield (92–96%) within short reaction time of 3–5 min. Electrophilic cyclization reaction

  室温离子液体氯化胆碱-草酸（ChCl：Ox）促进了，双（吲哚基）甲烷和双（4-羟基香豆素）甲烷的高效合成。ChCl：Ox（10 mol％）有效催化醛与苯肼的缩合，在3-5分钟的短时间内以高收率（92-96％）生成相应的。30mol％的ChCl∶Ox有效地促进了吲哚和4-羟基香豆素与芳族醛的亲电环化反应，在室温下以高收率得到了相应的双（吲哚基）芳基甲烷和双（4-羟基香豆素）甲烷。程序非常简单，无溶剂，完全消除了有毒酸催化剂的使用。ChCl：Ox是可生物降解的，可以循环使用，而不会损失产量。
• Zirconium oxide nano-catalyzed synthesis of pharmacologically important bis(indolyl)methanes: a highly efficient and mild approach
  作者：Komal Rathi、Om Shanker Tiwari、Varun Rawat、Jawahar L. Jat、Dinesh Kumar Yadav、Ved Prakash Verma

  DOI：10.1039/d4ob00324a

  日期：——

  We report herein a highly efficient and mild approach for synthesizing pharmacologically active bis(indolyl)methanes 3a–z, utilizing ZrO2 nanoparticles as a catalyst. The method involves a condensation reaction between indole and diverse aromatic aldehydes in acetonitrile under mild conditions. The ZrO2 nano-catalyst prepared via a co-precipitation method demonstrates exceptional efficacy, leading

  我们在此报告了一种利用 ZrO 2纳米粒子作为催化剂合成具有药理活性的双(吲哚基)甲烷3a-z的高效且温和的方法。该方法涉及吲哚与多种芳香醛在乙腈中在温和条件下进行缩合反应。通过共沉淀法制备的 ZrO 2纳米催化剂表现出卓越的功效，可实现目标双（吲哚基）甲烷3a–z的良好产率。通过底物筛选强调了该方法的多功能性，展示了其对各种芳香醛的适用性。
• A practical synthesis of bis(indolyl)methanes employing boric acid
  作者：Jhillu S. Yadav、Manoj K. Gupta、Ruchi Jain、Nagendra N. Yadav、Basi V. Subba Reddy

  DOI：10.1007/s00706-010-0355-8

  日期：2010.9

  A variety of aldehydes and ketones react rapidly with indoles in the presence of boric acid under solvent-free conditions to afford the corresponding bis(indolyl)methanes. Excellent yields and short reaction times together with the environmentally friendly nature of boric acid make this procedure useful and attractive to produce a variety of bis(indolyl)methanes. The use of boric acid makes it quite simple, more convenient, and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available boric acid.