3-[bis(1H-indol-3-yl)methyl]-4-chromenone | 957467-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-[bis(1H-indol-3-yl)methyl]-4-chromenone
• 英文别名: 3-[bis(indol-3-yl)methyl]chromone；(Chromon-3-yl)bis(indol-3-yl)methane；3-[bis(1H-indol-3-yl)methyl]chromen-4-one
• CAS: 957467-27-5
• 化学式: C₂₆H₁₈N₂O₂
• 分子量: 390.441
• InChiKey: ORUCYEQXUARSDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[bis(1H-indol-3-yl)methyl]-4-chromenone 在 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以80%的产率得到2-{4-[bis(indol-3-yl)methyl]-1H-pyrazol-3-yl}phenol
  参考文献：
  名称：

  Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis and some reactions of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones

  摘要：

  从 3-甲酰基色原酮出发，在无溶剂条件下与吲哚和 N-甲基吡咯反应，以较高收率获得了 (色原-3-基)双吲哚-3-基甲烷和 E-2-羟基-3-(1-甲基吡咯-2-亚甲基)色原-4-酮。由 (色原-3-基)双吲哚-3-基甲烷与碳酸胍和水合肼反应，在色原环结构的参与下，形成了相应的嘧啶和吡唑衍生物，并带有双吲哚-3-基甲基基团。 © 2008 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tet.2008.05.032
• 作为产物：
  描述：

  吲哚 、 色酮-3-甲醛 在 xanthan sulfuric acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以88%的产率得到3-[bis(1H-indol-3-yl)methyl]-4-chromenone
  参考文献：
  名称：

  Xanthan sulfuric acid: An efficient and biodegradable solid acid catalyst for the synthesis of bis(indolyl)methanes under solvent-free conditions

  摘要：

  研究发现黄原胶硫酸 (XSA) 是吲哚与芳香醛发生亲电取代反应的有效催化剂，可在室温、无溶剂条件下生成相应的双(吲哚基)甲烷。首次借助粉末 XRD、SEM-EDX 和 DSC-TGA 对催化剂进行了表征。这种绿色、新方法的吸引人的特点是优异的产品收率、清洁的反应曲线、催化剂的可重复使用性、能源可持续方案、简单的实验和更容易的后处理程序。

  DOI：

  10.1016/j.crci.2013.04.013

文献信息

• Synthesis and characterization of a tetracationic acidic organic salt and its application in the synthesis of bis(indolyl)methanes and protection of carbonyl compounds
  作者：Azim Ziyaei Halimehjani、Seyyed Emad Hooshmand、Elham Vali Shamiri

  DOI：10.1039/c5ra01422k

  日期：——

  A new tetracationic acidic organic salt (TCAOS) based on DABCO was prepared, characterized and applied as an eco-friendly, powerful and reusable catalyst for the synthesis of bis(indolyl)methanes from indoles and carbonyl compounds in water with high turnover frequency (TOF). Also, this catalyst was successfully applied for acetalization of carbonyl compounds with diols under solvent-free conditions

  制备了一种新的基于DABCO的四阳离子酸性有机盐（TCAOS），并表征为一种环保，功能强大且可重复使用的催化剂，用于在水中以高周转频率（TOF）从吲哚和羰基化合物合成双（吲哚基）甲烷。 ）。同样，该催化剂成功地用于无溶剂条件下用二醇对羰基化合物的缩醛化反应。
• Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones under solvent-free conditions
  作者：Vyacheslav Ya. Sosnovskikh、Roman A. Irgashev

  DOI：10.1016/j.tetlet.2007.08.078

  日期：2007.10

  (Chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones have been obtained in good yields from 3 -formylchromones on reaction with indoles and N-methylpyrrole under solvent-free conditions. (C) 2007 Elsevier Ltd. All rights reserved.

  (3-黄酮基)(吲哚-3-基)甲烷和E-2-羟基-3-(1-甲基吡咯-2-亚甲基)4-黄酮酮在无溶剂条件下，通过3-甲酰基黄酮与吲哚和N-甲基吡咯的反应，获得良好产率。© 2007 Elsevier Ltd. 保留所有权利。
• Oxalic acid dihydrate: Proline (LTTM) as a new generation solvent for synthesis of 3,3-diaryloxindole and chromone based bis(indolyl)alkanes: Green, chromatography free protocol
  作者：Dattatray Chandam、Abhijeet Mulik、Prasad Patil、Suryabala Jagdale、Dayanand Patil、Sandeep Sankpal、Madhukar Deshmukh

  DOI：10.1016/j.molliq.2015.02.036

  日期：2015.7

  The new green approach has been used for the reaction of indole with various carbonyl compounds. The attractive features of this protocol are the use of green reaction medium, good to excellent product yields, operational simplicity, easy workup procedures and the use of group assistance purification process avoiding chromatographic purification. This protocol is expected to find application in the combinatorial synthesis of biologically active compounds, since indole and chromone motifs have a broad spectrum of biological activities. (C) 2015 Elsevier B.V. All rights reserved.
• Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis and some reactions of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones
  作者：Vyacheslav Ya. Sosnovskikh、Roman A. Irgashev、Anna A. Levchenko

  DOI：10.1016/j.tet.2008.05.032

  日期：2008.7

  (Chromon-3-yl)bis(indol-3-yl)methanes and E-2-liydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones have been obtained in good yields from 3-formylchromones on reaction with indoles and N-methylpyrrole under solvent-free conditions. Reactions of (chromon-3-yl)bis(indol-3-yl)methanes with guanidine carbonate and hydrazine hydrate proceed with the participation of the chromone ring system and lead to the formation of the corresponding pyrimiclines and pyrazoles bearing the bis(indol-3-yl)methyl moiety. (C) 2008 Elsevier Ltd. All rights reserved.

  从 3-甲酰基色原酮出发，在无溶剂条件下与吲哚和 N-甲基吡咯反应，以较高收率获得了 (色原-3-基)双吲哚-3-基甲烷和 E-2-羟基-3-(1-甲基吡咯-2-亚甲基)色原-4-酮。由 (色原-3-基)双吲哚-3-基甲烷与碳酸胍和水合肼反应，在色原环结构的参与下，形成了相应的嘧啶和吡唑衍生物，并带有双吲哚-3-基甲基基团。 © 2008 Elsevier Ltd. 保留所有权利。
• Xanthan sulfuric acid: An efficient and biodegradable solid acid catalyst for the synthesis of bis(indolyl)methanes under solvent-free conditions
  作者：Zeba N. Siddiqui、Saima Tarannum

  DOI：10.1016/j.crci.2013.04.013

  日期：2013.9

  Résumé Xanthan sulfuric acid (XSA) is found to be an efficient catalyst for the electrophilic substitution reaction of indole with aromatic aldehydes to afford the corresponding bis(indolyl)methanes at room temperature under solvent-free conditions. The catalyst was characterized for the first time with the help of powder XRD, SEM–EDX and DSC–TGA. The attractive features of this green, new methodology are excellent yield of products, clean reaction profile, reusability of the catalyst, energy sustainable protocol, simple experimental and easier work-up procedures.

  研究发现黄原胶硫酸 (XSA) 是吲哚与芳香醛发生亲电取代反应的有效催化剂，可在室温、无溶剂条件下生成相应的双(吲哚基)甲烷。首次借助粉末 XRD、SEM-EDX 和 DSC-TGA 对催化剂进行了表征。这种绿色、新方法的吸引人的特点是优异的产品收率、清洁的反应曲线、催化剂的可重复使用性、能源可持续方案、简单的实验和更容易的后处理程序。