3-((1H-indol-3-yl)(4-nitrophenyl)methyl)-4-hydroxy-2H-chromen-2-one | 1191399-80-0

• 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)(4-nitrophenyl)methyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: (4-hydroxycoumarin-3-yl)(3-indolyl)(4-nitrophenyl)methane；4-hydroxy-3-[1H-indol-3-yl-(4-nitrophenyl)methyl]chromen-2-one
• CAS: 1191399-80-0
• 化学式: C₂₄H₁₆N₂O₅
• 分子量: 412.401
• InChiKey: JUHXGNQODMNIFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 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：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚 、 4-羟基香豆素 、 对硝基苯甲醛 在 L-脯氨酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.75h， 以74%的产率得到3-((1H-indol-3-yl)(4-nitrophenyl)methyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  升-脯氨酸催化的多组分一锅法合成宝石-diheteroarylmethane衍生物在室温下无溶剂条件下，使用容易的磨削操作

  摘要：

  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。

  DOI：

  10.1039/c3ra44568b

文献信息

• ‘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。
• Fe3O4@SiO2-SO3H-DABCO: A novel magnetically retrievable bifunctional catalyst for ecofriendly synthesis of diheteroarylmethanes
  作者：Archana Yadav、Pradeep Patil、Dattatray Chandam、Sushilkumar Jadhav、Anil Ghule、Shankar Hangirgekar、Sandeep Sankpal

  DOI：10.1016/j.molstruc.2021.130960

  日期：2021.12

  sustainable methodologies using green solvents, reusable catalysts and energy saving approaches is the need of time considering the growing stringent environmental regulations. The present study reports the novel three-step synthesis of magnetically separable Fe3O4@SiO2-SO3H-DABCO core-shell magnetic nanocomposite catalyst and evaluation of its catalytic efficiency involving the synthesis of structurally diverse

  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。
• 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.