3-(4-methoxyphenylamino)-1-(4-methoxyphenyl)-5-(p-tolyl)-1H-pyrrol-2(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(4-methoxyphenylamino)-1-(4-methoxyphenyl)-5-(p-tolyl)-1H-pyrrol-2(5H)-one
• 英文别名: 1-(4-Methoxyphenyl)-3-[(4-methoxyphenyl)amino]-5-(4-methylphenyl)-2,5-dihydro-1H-pyrrol-2-one；4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2-(4-methylphenyl)-2H-pyrrol-5-one
• 化学式: C₂₅H₂₄N₂O₃
• 分子量: 400.477
• InChiKey: OEKDYECETQFWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 1-butyl-1-methylpyrrolidinium hydrogen sulfate 作用下， 以 乙醇 为溶剂， 生成 3-(4-methoxyphenylamino)-1-(4-methoxyphenyl)-5-(p-tolyl)-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  1-Butyl-1-methylpyrrolidinium hydrogen sulfate-promoted preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives

  摘要：

  开发了一种便捷的制备方法，用于合成各种1,5-二芳基-3-(芳基氨基)-1H-吡咯-2(5H)-酮，这一方法由1-丁基-1-甲基吡咯烷铵氢磺酸促进，涉及醛与胺和乙基丙酮在常温条件下的环缩合反应。

  DOI：

  10.1007/s11164-012-0749-9

文献信息

• Organocatalytic Three-Component Reactions of Pyruvate, Aldehyde and Aniline by Hydrogen-Bonding Catalysts
  作者：Xin Li、Hui Deng、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.200800491

  日期：2008.9

  Hydrogen-bonding catalysts have been found to catalyze one-pot three-component reactions of pyruvate, anilines and aldehydes to afford versatile 3-amino-1,5-dihydro-2H-pyrrol-2-ones in high yields. Both, thioureas and phosphoric acids are viable catalysts for these reactions and have comparable activity. The corresponding chiral thioureas and phosphoric acids have also been used in these three-component

  已发现氢键催化剂可催化丙酮酸、苯胺和醛的一锅三组分反应，以高产率提供多功能的 3-氨基-1,5-二氢-2H-吡咯-2-酮。硫脲和磷酸都是这些反应的可行催化剂，并且具有相当的活性。相应的手性硫脲和磷酸也已用于这些三组分反应中，以高产率和中等对映选择性得到吡咯-2-酮。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008 )
• Uncatalyzed synthesis of 3-amino-1,5-dihydro-2H-pyrrol-2-ones
  作者：Hamid Reza Shaterian、Mohammad Ranjbar

  DOI：10.1007/s11164-013-1102-7

  日期：2014.5

  Uncatalyzed one-pot pseudo-four-component reaction of ethyl pyruvate, anilines, and aldehydes in n-hexane as solvent, under reflux, affords a variety of 3-amino-1,5-dihydro-2H-pyrrol-2-ones in high yield. n-Hexane is an excellent driving force in preparation of the desired products. These compounds have biological and pharmacological properties and are also used in medicinal chemistry. Use of a non-toxic and inexpensive solvent, simple and efficient synthesis, clean work-up, and high yields of the products are the advantages of this method. We report the first catalyst-free method for synthesis this class of compounds.

  丙酮酸乙酯、苯胺和醛在正己烷为溶剂、回流条件下进行非催化的单锅伪四组份反应，可高产多种 3-氨基-1,5-二氢-2H-吡咯-2-酮。这些化合物具有生物和药理特性，也可用于药物化学。使用无毒且廉价的溶剂、简单高效的合成、清洁的操作以及高产率是该方法的优点。我们报告了合成这类化合物的第一种无催化剂方法。
• Triethylammonium Hydrogen Sulfate as a Catalyst for the Preparation of 1,5-diaryl-3-(arylamino)-1<i>H</i>-pyrrol-2(5<i>H</i>)-one derivatives
  作者：Mohammad Reza Mohammad Shafiee、Batool Hojati Najafabadi、Majid Ghashang

  DOI：10.3184/174751911x13191347034936

  日期：2011.11

  Triethylammonium hydrogen sulfate [Et3NH][HSO4]) has been used as an efficient acidic ionic liquid catalyst for the preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones at room temperature. The present methodology offers the advantages of good yields, a simple procedure, shorter reaction times and mild condition. The products were purified without resorting to chromatography.

  三乙基硫酸氢铵 [Et3NH][HSO4]) 已被用作一种有效的酸性离子液体催化剂，用于在室温下制备 1,5-二芳基-3-(芳基氨基)-1H-吡咯-2(5H)-酮。本方法具有收率高、操作简单、反应时间短、条件温和等优点。产物不用色谱法纯化。
• Efficient synthesis of 3-arylaminopyrroline-2-ones by the tandem reaction of anilines and β,γ-unsaturated α-ketoesters
  作者：Yan-Chao Wu、Li Liu、Dong Wang、Yong-Jun Chen

  DOI：10.1002/jhet.5570430421

  日期：2006.7

  A concise and efficient synthetic approach to 3-arylaminopyrroline-2-ones from anilines and β,γ-unsaturated α-ketoesters in boiling dichloromethane has been developed. This protocol possesses many advantages such as short reaction time, high isolated yields, and expanding substrate scopes. According to the isolated intermediates and controlled reactions, the reaction was tentatively proposed to involve

  已开发出一种简洁有效的合成方法，可在沸腾的二氯甲烷中从苯胺和β，γ-不饱和α-酮酸酯合成3-芳基氨基吡咯啉-2-酮。该方案具有许多优点，例如反应时间短，分离产率高和扩大了底物范围。根据分离的中间体和受控反应，初步提出该反应涉及迈克尔加成/缩合和随后的分子内环化。通过各种光谱数据如X射线晶体学分析清楚地证实了标题化合物的结构。
• 1-Butyl-1-methylpyrrolidinium hydrogen sulfate-promoted preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
  作者：Majid Ghashang

  DOI：10.1007/s11164-012-0749-9

  日期：2013.5

  A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1-methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions. A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1-methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions.

  开发了一种便捷的制备方法，用于合成各种1,5-二芳基-3-(芳基氨基)-1H-吡咯-2(5H)-酮，这一方法由1-丁基-1-甲基吡咯烷铵氢磺酸促进，涉及醛与胺和乙基丙酮在常温条件下的环缩合反应。