3-((1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-2H-chromen-2-one | 1191399-79-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-((1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 4-hydroxy-3-[1H-indol-3-yl(phenyl)methyl]chromen-2-one
• CAS: 1191399-79-7
• 化学式: C₂₄H₁₇NO₃
• 分子量: 367.404
• InChiKey: CLAIBUBQUKZUFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 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：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 4-羟基香豆素 、 苯甲醛 在 DABCO immobilized on silica-coated magnetic nano-Fe₃O₄ core-shell nanocomposite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以93%的产率得到3-((1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Fe 3 O 4 @SiO 2 -SO 3 H-DABCO：一种新型磁性可回收双功能催化剂，用于二杂芳基甲烷的生态友好合成

  摘要：

  考虑到日益严格的环境法规，开发使用绿色溶剂、可重复使用催化剂和节能方法的可持续方法是需要时间的。本研究报告了磁性可分离 Fe 3 O 4 @SiO 2 -SO 3 H-DABCO 核壳磁性纳米复合催化剂的新型三步合成及其催化效率评估，包括通过一锅反应合成结构多样的二杂芳基甲烷乙醇水溶液中吲哚、芳醛和 4-羟基香豆素的浓度 (50:50 v/v) 在环境条件下。催化剂可以连续循环六次，催化活性或产品产率没有显着变化。生态友好的合成方法提供了几个优点，例如使用绿色溶剂系统、环境反应条件、更短的反应时间、优异的收率和易于使用外部磁铁分离催化剂。

  DOI：

  10.1016/j.molstruc.2021.130960

文献信息

• l-Proline catalyzed multicomponent one-pot synthesis of gem-diheteroarylmethane derivatives using facile grinding operation under solvent-free conditions at room temperature
  作者：Goutam Brahmachari、Suvankar Das

  DOI：10.1039/c3ra44568b

  日期：——

  straightforward L-proline catalyzed one-pot synthesis of a series of biologically relevant gem-(β-dicarbonyl)arylmethanes has been developed via a three-component reaction between indoles, aldehydes and C–H activated acids by grinding them together under solvent-free conditions at room temperature. Mild reaction conditions, high atom-economy, good yields, and eco-friendliness are some of the salient

  通过吲哚，醛和CHH活化酸之间的三组分反应，通过在以下条件下将它们研磨在一起，开发了一种高效且直接的L-脯氨酸催化一锅合成一系列生物学相关的宝石-（β-二羰基）芳基甲烷的方法。室温下无​​溶剂条件。温和的反应条件，高原子经济性，良好的收率和生态友好性是本方案的一些重要特征。
• ‘Naked-eye’ colorimetric/fluorimetric detection of F⁻ ions by biologically active 3-((1H-indol-3-yl)methyl)-4-hydroxy-2H-chromen-2-one derivatives
  作者：Shaily Shaily、Ajay Kumar、Sumit Kumar、Naseem Ahmed

  DOI：10.1039/c6ra24597h

  日期：——

  An improved synthetic protocol has been developed to construct highly functionalized heterologous alkyl and benzyl indolyl-coumarin derivatives using a rapid, catalyst-free and solvent-free one-pot three-component reaction of indole, aldehyde and 4-hydroxy-coumarin.

  一种改进的合成方案已经开发出来，可以使用快速、无催化剂和无溶剂的一锅三组分反应，构建高度功能化的异源烷基和苄基吲哚基香豆素衍生物，反应物包括吲哚、醛和4-羟基香豆素。
• InCl3 catalyzed three-component synthesis of α-benzylamino coumarins and diketones
  作者：Pallavi Rao、Saidulu Konda、Javed Iqbal、Srinivas Oruganti

  DOI：10.1016/j.tetlet.2012.07.098

  日期：2012.9

  A convenient and practical InCl3 catalyzed three-component reaction of 4-hydroxy coumarin/1,3 diones, aromatic aldehyde, and secondary amine for the synthesis of alpha-benzylamino coumarins and diketones in good yields has been reported. (c) 2012 Elsevier Ltd. All rights reserved.
• A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes
  作者：Giovanni Appendino、Lavinia Cicione、Alberto Minassi

  DOI：10.1016/j.tetlet.2009.05.033

  日期：2009.10

  The reaction of aldehydes with beta-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Selective One-Pot Coupling Reaction of Indole, Aromatic Aldehydes, and 4-hydroxycoumarin Using Copper Octoate as a Homogeneous Catalyst
  作者：Farnoush Mousavizadeh、Rahim Hekmatshoar、Seyed Yahya Shirazi Beheshtiha、Reyhaneh Rahnamafar

  DOI：10.1080/00397911.2013.862723

  日期：2014.5.19

  A facile protocol for the one-pot, multicomponent reaction of indole, 4-hydroxycoumarin, and aromatic aldehydes was developed using copper octoate as an inexpensive, commercially available, and efficient catalyst. This highly selective reaction eliminates the formation of homodimeric by-products (bisindoles and biscoumarins) and selectively results in the formation of heterodimeric adducts containing both indole and coumarin heterocycles.