methyl 4-(3-nitroanilino)-5-oxo-2-phenyl-2H-furan-3-carboxylate | 1415958-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(3-nitroanilino)-5-oxo-2-phenyl-2H-furan-3-carboxylate
• CAS: 1415958-78-9
• 化学式: C₁₈H₁₄N₂O₆
• 分子量: 354.319
• InChiKey: WRZXLLQMTNSBKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲醛 、 丁炔二酸二甲酯 、 间硝基苯胺 在 1-甲基-3-丁基咪唑硫酸氢盐 作用下， 以 neat (no solvent) 为溶剂， 以81%的产率得到methyl 4-(3-nitroanilino)-5-oxo-2-phenyl-2H-furan-3-carboxylate
  参考文献：
  名称：

  Brøsted Acidic Ionic Liquid ([Bmim]Hso4) Promoted Cyclocodensation Reaction: Synthesis of 3,4,5-Substituted Furan-2(5h)-Ones

  摘要：

  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。

  DOI：

  10.13005/ojc/310424

文献信息

• 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。
• Application of Silica Gel-supported Polyphosphoric Acid (PPA/SiO&lt;sub&gt;2&lt;/sub&gt;) as a Reusable Solid Acid Catalyst for One-Pot Multi-Component Synthesis of 3,4,5-substituted furan-2(5H)-ones
  作者：Razieh Doostmohammadi、Nourallah Hazeri

  DOI：10.2174/1570178611310030010

  日期：2013.4.1

  3,4,5-substituted furan-2(5H)-ones were One-Pot Multi-Component synthesized by the reaction of aldehydes, amines and dialkyl acetylenedicarboxylates using silica gel-supported polyphosphoric acid (PPA/SiO2) at room temperature. This reaction provides a convenient and efficient synthetic method of furan-2(5H)-one derivatives, and also reusability of catalyst.

  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。
• 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
• An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate
  作者：Razieh Doostmohammadi、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani

  DOI：10.1016/j.cclet.2013.06.004

  日期：2013.10

  A facile one-pot synthesis of 3,4,5-substituted furan-2(5H)-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed. (C) 2013 Malek Taher Maghsoodlou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.