3,3'-(anthracene-10-yl-methanediyl)bisindole

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3,3'-(anthracene-10-yl-methanediyl)bisindole
• 英文别名: 3-((anthracen-9-yl)(1H-indol-3-yl)methyl)-1H-indole；3,3′-(anthracene-9-ylmethylene)bis(1H-indole)；3,3'-(anthracen-9-ylmethylene)bis(1H-indole)；3-[anthracen-9-yl(1H-indol-3-yl)methyl]-1H-indole
• 化学式: C₃₁H₂₂N₂
• 分子量: 422.529
• InChiKey: RSZLRQUBNOSTIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  7.0
• 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：

  四丁基硫酸氢铵 、 3,3'-(anthracene-10-yl-methanediyl)bisindole 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Indole-based distinctive chemosensors for ‘naked-eye’ detection of CN and HSO₄⁻, associated with hydrogen-bonded complex and their DFT study

  摘要：

  Colorimetric detection of anions (HSO4- and CN-) was achieved via analyte triggered colour changing of the dipodal and tripodal sensors in CH3CN-H2O (1:1). The sensors exhibited very sharp visual colour changes and fluorescence quenching-enhancing effect upon addition of the HSO4- and CN-. The large downfield shift of the NH proton signals in H-1-NMR complexation studies and quantum chemical DFT calculations proved the formation of hydrogen-bonded complexes where no proton transfer mechanism was found.

  DOI：

  10.1080/10610278.2015.1092534
• 作为产物：
  描述：

  2-碘苯胺 在 silver hexafluoroantimonate 、 potassium acetate 、 palladium diacetate 、 三苯基膦 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 5.5h， 生成 3,3'-(anthracene-10-yl-methanediyl)bisindole
  参考文献：
  名称：

  通过顺序的Sonogashira偶联和2-碘代苯胺的环异构化/ C3-官能化反应一锅合成2,2'-二取代的二吲哚基甲烷（DIM）

  摘要：

  已经开发了Pd（II）-Ag（I）催化的二吲哚基甲烷的高效合成。此转化过程包括一锅顺序的Sonogashira偶联（和去甲硅烷基化），然后进行2-碘苯胺的环异构化/ C3官能化。六个新债券（四个CC和两个CN）以一种底池形式形成。在温和的反应条件下，以优异的收率（高达94％）获得了各种二吲哚基甲烷，该策略也适用于克规模的合成。将产物转化为各种合成有用的化合物。

  DOI：

  10.1039/c7ob01701d

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。
• One-pot conversion of aromatic compounds to the corresponding bis(indolyl)methanes by the Vilsmeier–Haack reaction
  作者：Hojat Veisi、Meral Ataee、Pegah Darabi-Tabar、Effat Amiri、Ali Reza Faraji

  DOI：10.1016/j.crci.2013.09.011

  日期：2014.4

  Résumé Various electron-rich aromatics could be smoothly converted into the corresponding bis(indolyl)methanes in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with indole at room temperature. The present article is the first report on a novel metal-free one-pot method for the preparation of bis(indolyl)methanes from electron-rich aromatics.

  摘要 通过电子丰富的芳香族化合物与POCl3和DMF的处理，随后在室温下与吲哚反应，可以顺利地将多种电子丰富的芳香族化合物转化为相应的二(吲哚基)甲烷，产率良好至中等。本文首次报道了一种新颖的无金属一步法，用于从电子丰富的芳香族化合物制备二(吲哚基)甲烷。
• 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。
• Lithium Perchlorate Catalyzed Reactions of Indoles: An Expeditious Synthesis of Bis(indolyl)methanes
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Ch. V. S. R. Murthy、G. Mahesh Kumar、Ch. Madan

  DOI：10.1055/s-2001-12777

  日期：——

  Lithium perchlorate is found to catalyze efficiently the electrophilic substitution reactions of indoles with aldehydes and ketones in diethyl ether to afford the corresponding bis(indolyl)methanes in high yields. LiOTf is also found to be an efficient catalyst for the synthesis of these compounds.

  发现高氯酸锂有效地催化吲哚与醛和酮在乙醚中的亲电取代反应，以高产率提供相应的双（吲哚基）甲烷。LiOTf 也被发现是合成这些化合物的有效催化剂。
• An Efficient and Practical Process for the Synthesis of Bis(indolyl)methanes Catalyzed by Zirconium Tetrachloride
  作者：Yong-Mei Wang、Zhan-Hui Zhang、Liang Yin

  DOI：10.1055/s-2005-869959

  日期：——

  Zirconium tetrachloride is used as a catalyst for the elec- trophilic substitution reaction of indole with aldehydes or ketones at ambient temperature to afford the corresponding bis(indolyl)meth- anes in good to excellent yields.

  四氯化锆用作吲哚与醛或酮在环境温度下进行电取代反应的催化剂，以良好至优异的产率提供相应的双（吲哚基）甲烷。