bis(indol-3-yl)-2,6-dichlorophenylmethane | 942518-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: bis(indol-3-yl)-2,6-dichlorophenylmethane
• 英文别名: 3,3'-(2,6-dichlorophenylmethanediyl)bisindole；3,3'-(2,6-dichlorophenyl)methylenebisindole；3-((2,6-Dichlorophenyl)(1h-indol-3-yl)methyl)-1h-indole；3-[(2,6-dichlorophenyl)-(1H-indol-3-yl)methyl]-1H-indole
• CAS: 942518-07-2
• 化学式: C₂₃H₁₆Cl₂N₂
• 分子量: 391.299
• InChiKey: WOLFNHIQAIMAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  吲哚 、 3,5-二氯苯甲醛 在 H₆P₂W₁₈O₆₂*24H₂O 作用下， 反应 0.33h， 以75%的产率得到bis(indol-3-yl)-2,6-dichlorophenylmethane
  参考文献：
  名称：

  An efficient and green synthetic protocol for the preparation of bis(indolyl)methanes catalyzed by H6P2W18O62·24H2O, with emphasis on the catalytic proficiency of Wells-Dawson versus Keggin heteropolyacids

  摘要：

  A simple, atom economy, and a highly well-organized green protocol has been developed for the synthesis of bis(indolyl)methanes. Wells-Dawson diphosphooctadecatungsticacid (H6P2W18O62 center dot 24H(2)O) was employed as a proficient, a highly water tolerant, and green heteropolyacid catalyst for the electrophilic substitution reactions of indole with various aldehydes and ketones to afford the corresponding bis(indolyl)methane derivatives under solvent-free condition. Presumably, discrepancies observed in the reactivity patterns of various heteropolyacids would be explained concerning differences in the acidity, structural diversity, and dissimilarities in the approach of the substrates to the bulk of the heteropolyacid catalysts. It is confirmed that the identity of the catalyst was retained almost completely during the catalytic reaction. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.09.029

文献信息

• BF₃-grafted Fe₃O₄@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)
  作者：Iman Radfar、Maryam Kazemi Miraki、Leila Ghandi、Naghmeh Esfandiary、Sepideh Abbasi、Meghdad Karimi、Akbar Heydari

  DOI：10.1002/aoc.4431

  日期：2018.8

  core and grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3‐Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT‐IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one

  当前的论文表示将蔗糖固定在Fe 3 O 4核上并将三氟化硼（BF 3）接枝到新表面上。在二氢喹唑啉酮（DHQZs）和双（3-吲哚基）甲烷（BIM）的合成中，作为两种卓有成效的药物结构，测试了这些纳米颗粒的催化活性。对这种新型纳米颗粒（NP）进行了酸性容量，FT-IR，XRD，VSM，TGA和SEM-EDX测试。与以前报道的磺化同系物相比，催化剂每1克NP的酸容量更高。
• Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
  作者：Wayland E. Noland、Honnaiah Vijay Kumar、Grant C. Flick、Cole L. Aspros、Jong Hyeon Yoon、Andre C. Wilt、Nasim Dehkordi、Sheng Thao、Andrew K. Schneerer、Siming Gao、Kenneth J. Tritch

  DOI：10.1016/j.tet.2017.05.061

  日期：2017.7

  Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields

  水合硫酸铁[Fe 2（SO 4）3 · x H 2 O]被发现是双吲哚或三吲哚与脂族或芳基醛和酮（包括甲基和乙基烷基酮，甲基芳基酮）缩合的有效催化剂，环酮和4-chromanones的产率为19-96％。从吲哚-3-甲醛或3-甲基吲哚获得三吲哚和2,2'-亚烷基双吲哚，产率为72–84％。总共使用了43种底物，得到33种双吲哚，3种三吲哚和一种2：2产物。其中有十七个是新的。用Fe 2（SO 4）3 · x加热乙醇悬浮液可获得最佳结果。H 2 O负载量为60 mg / mmol亲电试剂。反应时间通常为1-4小时，而受阻亲电试剂则需要8-24小时。这些条件足够强以促进吲哚与底物的2：1缩合，而不会形成高阶副产物，几乎没有例外。该策略的特征在于催化剂对各种官能团的耐受性，易于获得的起始原料，简单的操作，温和的反应条件以及对环境友好。
• Nano n-propylsulfonated γ-Fe2O3 (NPS-γ-Fe2O3) as a magnetically recyclable heterogeneous catalyst for the efficient synthesis of 2-indolyl-1-nitroalkanes and bis(indolyl)methanes
  作者：Sara Sobhani、Roya Jahanshahi

  DOI：10.1039/c3nj40899j

  日期：——

  Nano n-propylsulfonated γ-Fe2O3 (NPS-γ-Fe2O3) was used as a new magnetically recyclable heterogeneous catalyst for the efficient synthesis of indole derivatives, such as 2-indolyl-1-nitroalkanes and bis(indolyl)methanes.

  纳米n-丙基磺酸化的γ-Fe2O3 (NPS-γ-Fe2O3) 被用作一种新的磁性可回收异相催化剂，用于高效合成吲哚衍生物，如2-吲哚基-1-硝基烷和双(吲哚基)甲烷。
• An eco-friendly procedure for the efficient synthesis of bis(indolyl)methanes in aqueous media
  作者：Sara Sobhani、Elham Safaei、Ali-Reza Hasaninejad、Soodabeh Rezazadeh

  DOI：10.1016/j.jorganchem.2009.05.004

  日期：2009.8

  A new, convenient and high yielding procedure for the preparation of bis(indolyl)methanes in water by electrophilic substitution reaction of indoles with different carbonyl compounds in the presence of a catalytic amount of [Cu(3,4-tmtppa)](MeSO4)4 (1 mol%) as a highly stable and reusable catalyst is described. This procedure has also been applied successfully for the preparation of bis(pyrazole-5-ols)

  在催化量[Cu（3,4-tmtppa）]（MeSO 4）存在下，吲哚与不同羰基化合物的亲电取代反应，用于制备水中的双（吲哚基）甲烷的新方法，方便且高收率）描述了4（1 mol％）作为高度稳定和可重复使用的催化剂。该方法也已经成功地用于制备双（吡唑-5-醇）和二吡咯甲烷。
• Cu-isatin schiff base complex supported on magnetic nanoparticles as an efficient and recyclable catalyst for the synthesis of bis(indolyl)methanes and bis(pyrazolyl)methanes in aqueous media
  作者：Sara Sobhani、Solmaz Asadi、Mehri Salimi、Farzaneh Zarifi

  DOI：10.1016/j.jorganchem.2016.08.021

  日期：2016.11

  Schiff base supported on γ-Fe2O3 as a new catalyst was synthesized and characterized by different methods such as SEM, TEM, XRD, TGA, FT-IR, ICP, VSM and CHN analysis. It was used as a reusable heterogeneous catalyst for the efficient synthesis of bis(indolyl)methanes (TON = 320–392) and bis(pyrazolyl)methanes (TON = 340–388) in aqueous media. The catalyst was easily removed from the reaction mixture

  的Cu-靛红支撑在γ-铁Schiff碱2 ö 3作为新的催化剂的合成和表征通过不同的方法如SEM，TEM，X射线衍射，TGA，FT-IR，ICP，VSM和CHN分析。它被用作可重复使用的非均相催化剂，用于在水性介质中高效合成双（吲哚基）甲烷（TON = 320–392）和双（吡唑基）甲烷（TON = 340–388）。使用外部磁体可以很容易地从反应混合物中除去催化剂，并重复使用八次而不会显着降低其反应活性。