2-hydroxy-3-[(phenylamino)(p-tolyl)methyl]naphthalene-1,4-dione | 1259091-72-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-hydroxy-3-[(phenylamino)(p-tolyl)methyl]naphthalene-1,4-dione
• CAS: 1259091-72-9
• 化学式: C₂₄H₁₉NO₃
• 分子量: 369.42
• InChiKey: GGUHKIHAVZNNOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 对甲基苯甲醛 、 苯胺 在 zirconyl chloride octahydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 7.0h， 以80%的产率得到2-hydroxy-3-[(phenylamino)(p-tolyl)methyl]naphthalene-1,4-dione
  参考文献：
  名称：

  ZrOCl2·8H2O as an efficient catalyst for the synthesis of dibenzo [b,i]xanthene-tetraones and fluorescent hydroxyl naphthalene-1,4-diones

  摘要：

  报道了一种高效的、环境友好的合成方法，用于在无溶剂条件下，借助少量廉价且环保的催化剂ZrOCl2·8H2O，高活性地合成二苯并[b,i]咕吨四酮和荧光性羟基萘-1,4-二酮。

  DOI：

  10.1007/s11164-013-1413-8

文献信息

• Application of cobalt phthalocyanine as a nanostructured catalyst in the synthesis of biological henna-based compounds
  作者：Mohammad Dashteh、Maliheh Safaiee、Saeed Baghery、Mohammad Ali Zolfigol

  DOI：10.1002/aoc.4690

  日期：2019.4

  The present investigation describes synthesis of a good range of henna‐based compounds in the presence of novel nano cobalt phthalocyanine like molten salt (tetra‐2,3‐pyridiniumporphyrazinato cobalt tribromomethanide) [Co (TPPABr)]CBr3 as an efficient, recyclable and thermally stable heterogeneous catalyst.

  本研究描述了新型纳米酞菁钴的存在等熔融盐（四甲基-2,3- pyridiniumporphyrazinato钴tribromomethanide）[CO（TPPABr）] CBR一个良好的范围的基于指甲花的化合物的合成3作为一种高效，可回收和热稳定的非均相催化剂。
• Synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a three-component reaction in water
  作者：Minoo Dabiri、Zeinab Noroozi Tisseh、Ayoob Bazgir

  DOI：10.1016/j.dyepig.2010.09.004

  日期：2011.4

  An efficient one-pot synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a simple, atom-economical and three-component reaction of 2- hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic or carbocyclic amines in the presence of a catalytic amount of InCl3 in refluxing water is reported. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental

  通过存在下存在的2-羟基萘-1,4-二酮，芳族醛和杂环或碳环胺的简单，原子经济和三组分反应，可以有效地一锅合成荧光羟基萘-1,4-二酮衍生物报道了在回流水中催化量的InCl 3的含量。化合物的结构通过IR，1 H NMR，13确认。13 C NMR和元素分析。在甲醇中测量了UV-可见光吸收系数，最大波长和荧光发射波长。产品在溶液中发出绿色荧光（546-560 nm）时发出荧光。该方法的优点是反应条件温和，产物收率高，操作简单且后处理程序容易。这些非常干净的反应的后处理仅涉及使用EtOH进行过滤和简单的洗涤步骤。
• Design and characterization of Dendrimer of MNPs as a novel, heterogeneous and reusable nanomagnetic organometallic catalyst for one‐pot synthesis of hydroxyl naphthalene‐1,4‐dione derivatives under solvent‐free conditions
  作者：Fouziyeh Mollazehi、Hamid Reza Shaterian

  DOI：10.1002/aoc.4183

  日期：2018.3

  activity of the catalyst for one‐pot, efficient and facile synthesis of 2‐hydroxy‐1,4‐naphthoquinone derivatives via a three‐component condensation reaction of 2‐hydroxynaphthalene‐1,4‐dione, aromatic aldehydes and aniline derivatives. High yields of products, short reaction times, waste‐free, mild, ambient and solvent‐free reaction conditions are advantages of this protocol. Also, the catalyst can be easily

  成功合成了新型超酸性磁性纳米粒子。这个树枝状聚合物的磺酸官能化γ-的Fe制备2 ö 3所描述的磁性核-壳纳米颗粒的二氧化硅作为新的可恢复和异构纳米催化剂。使用多种技术对新催化剂进行表征，例如扫描电子显微镜（SEM），能量色散谱（EDS）和热重分析（TGA）。此外，我们已经研究了催化剂的催化活性为一锅，高效，简便合成2-羟基-1,4-萘醌衍生物的经由2-羟基萘-1,4-二酮，芳族醛和苯胺衍生物的三组分缩合反应。该方案的优点是产品产量高，反应时间短，无浪费，温和，环境和无溶剂的反应条件。而且，该催化剂可以容易地通过外磁回收并重复使用几次而不会显着降低其催化活性。
• L-Proline as a Recyclable Organocatalyst for the Preparation of Hydroxy‐Substituted Naphthalene‐1,4‐diones
  作者：T. S. Daloee、F. K. Behbahani、G. B. Marandi

  DOI：10.1134/s1070428022090202

  日期：2022.9

  Abstract An efficient method for the synthesis of hydroxy‐substituted naphthalene-1,4-dione derivatives using L-proline as a green organocatalyst under reflux conditions in ethanol is described. A simple procedure, high yields, short reaction time, safety, and reusability of the catalyst are advantages of the described protocol.

  摘要 描述了一种在乙醇中回流条件下使用 L-脯氨酸作为绿色有机催化剂合成羟基取代的 1,4-二酮衍生物的有效方法。简单的程序、高产率、短反应时间、安全性和催化剂的可重复使用性是所述协议的优点。
• Synthesis of 2-hydroxy-1,4-naphthoquinone derivatives via a three-component reaction catalyzed by nanoporous MCM-41
  作者：Soroush Shaabani、Mohammad Reza Naimi-Jamal、Ali Maleki

  DOI：10.1016/j.dyepig.2015.06.013

  日期：2015.11

  A one-pot procedure for synthesis of hydroxyl naphthalene-1,4-dione derivatives via a three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic or carbocyclic amines is developed. MCM-41 nanoporous catalyst is effective, easy recovery, reusable and makes work-up easy. This approach is clean and environmentally friendly. The structures of the new compounds were confirmed by FT-IR, H-1 NMR,C-13 NMR, and elemental analysis. (C) 2015 Elsevier Ltd. All rights reserved.