ethyl 2,5-dihydro-2-(4-methoxyphenyl)-5-oxo-4-(phenylamino)furan-3-carboxylate | 1174434-68-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2,5-dihydro-2-(4-methoxyphenyl)-5-oxo-4-(phenylamino)furan-3-carboxylate
• 英文别名: ethyl 4-anilino-2-(4-methoxyphenyl)-5-oxo-2H-furan-3-carboxylate
• CAS: 1174434-68-4
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: QEJLBMOVEZIACC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 苯胺 、 丁炔二酸二乙酯 在 silica gel supported polyphosphoric acid 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以62%的产率得到ethyl 2,5-dihydro-2-(4-methoxyphenyl)-5-oxo-4-(phenylamino)furan-3-carboxylate
  参考文献：
  名称：

  Application of Silica Gel-supported Polyphosphoric Acid (PPA/SiO₂) as a Reusable Solid Acid Catalyst for One-Pot Multi-Component Synthesis of 3,4,5-substituted furan-2(5H)-ones

  摘要：

  使用硅胶支撑的聚磷酸（PPA/SiO2）在室温下通过醛、胺和乙炔二羧酸二烷基酯的反应，单锅多组分合成了 3、4、5-取代的呋喃-2(5H)-酮。 该反应为呋喃-2(5H)-酮衍生物的合成提供了一种便捷高效的方法，而且催化剂可重复使用。

  DOI：

  10.2174/1570178611310030010

文献信息

• Brøsted Acidic Ionic Liquid ([Bmim]Hso4) Promoted Cyclocodensation Reaction: Synthesis of 3,4,5-Substituted Furan-2(5h)-Ones
  作者：Sajjad Salahi、Malek Maghsoodlou、Nourallah Hazeri

  DOI：10.13005/ojc/310424

  日期：2015.12.30

  1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4: an acidic ionic liquid was used as a catalyst for the synthesis of heterocyclic compounds 3,4,5-substituted furan-2(5H)-ones from aniline derivatives, dialkyl acetylenedicarboxylates and aromatic aldehydes at 75 °C. Solvent-free conditions, shorter reaction time, and good yields (71-94%) are some of advantages.

  1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4: 一种酸性离子液体被用作催化剂，用于在 75 °C 下从苯胺衍生物、乙炔二羧酸二烷基酯和芳香醛合成杂环化合物 3、4、5-取代的呋喃-2(5H)-酮。该方法具有无溶剂条件、反应时间短、收率高（71-94%）等优点。
• Acidic ionic liquid N-methyl 2-pyrrolidonium hydrogen sulfate as an efficient catalyst for the one-pot multicomponent preparation of 3,4,5-substituted furan-2(5H)-ones
  作者：Sajjad Salahi、Malek Taher Maghsoodlou、Nourallah Hazeri、Fahimeh Movahedifar、Razieh Doostmohammadi、Mojtaba Lashkari

  DOI：10.1007/s11164-014-1754-y

  日期：2015.9

  We have developed an efficient method for the synthesis of 3,4,5-substituted furan-2(5H)-ones via one-pot, three-component condensation reaction of aldehydes, amines, and dialkyl acetylenedicarboxylates using acidic ionic liquid catalyst (N-methyl 2-pyrrolidonium hydrogen sulfate ([H-NMP]HSO4)). This reaction benefits from simple, inexpensive, and straightforward procedure, an environmental friendly method, and high yields.

  我们利用酸性离子液体催化剂（N-甲基 2-吡咯烷酮硫酸氢盐（[H-NMP]HSO4）），通过醛、胺和乙炔二甲酸二烷基酯的单锅三组分缩合反应，开发了一种合成 3、4、5-取代的呋喃-2(5H)-酮的高效方法。该反应具有操作简单、成本低廉、过程直接、环境友好和产率高等优点。
• Efficient One-Pot Three-Component Synthesis of 3,4,5-Substituted Furan-2(5<i>H</i>)-ones Catalyzed Watermelon Juice
  作者：Belghais Adrom、Malek Taher Maghsoodlou、Mojtaba Lashkari、Nourallah Hazeri、Razieh Doostmohammadi

  DOI：10.1080/15533174.2014.988230

  日期：2016.3.3

  A simple, efficient, and environmentally benign protocol for the synthesis of 3,4,5-substituted furan-2(5H)-ones has been achieved using extract of watermelon as a natural catalyst. We found, for the first time, that the extract of watermelon could effectively catalyze The condensation reaction of aldehydes, amines, and dialkyl acetylenedicarboxylates to 3,4,5-substituted furan-2(5H)-ones in excellent

  使用西瓜提取物作为天然催化剂，已经实现了一种简单，高效且环境友好的合成3,4,5-取代的呋喃2（5 H）-1的方案。我们首次发现，西瓜提取物可以在温和条件下以优异的收率有效催化醛，胺和乙酰二羧酸二烷基酯的缩合反应生成3,4,5-取代的呋喃-2（5 H）-酮。 。低成本，催化剂的容易获得和简单的反应条件表明本方法可用于大规模制备。
• Acetic acid as an efficient catalyst for the one-pot preparation of 3,4,5-substituted furan-2(5H)-ones
  作者：Razieh Doostmohammadi、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani

  DOI：10.1007/s11164-012-0922-1

  日期：2013.11

  Abstract The three-component condensation reaction of aldehydes, amines,and dialkyl acetylenedicarboxylates was conducted, leading to the production of 3,4,5-substituted furan-2(5H)-ones. This reaction is performed in the presence of acetic acid as a cheap and readily available catalyst at room temperature. Graphical Abstract  

  摘要 进行了醛，胺和乙炔基二羧酸二烷基酯的三组分缩合反应，从而生成了3,4,5-取代的呋喃-2（5H）-一。该反应在乙酸存在下作为廉价且容易获得的催化剂在室温下进行。 图形概要
• Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using β-cyclodextrin as reusable catalyst
  作者：S. Narayana Murthy、B. Madhav、A. Vijay Kumar、K. Rama Rao、Y.V.D. Nageswar

  DOI：10.1016/j.tet.2009.04.081

  日期：2009.7

  3,4,5-Substituted furan-2(5H)-one derivatives were synthesized by using beta-cyclodextrin as a catalyst in water via biomimetic approach. beta-Cyclodextrin can be recovered and reused. (C) 2009 Elsevier Ltd. All rights reserved.