5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-[(4-methoxyphenyl)amino]-1H-pyrrol-2(5H)-one | 1075727-71-7

• 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: 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-[(4-methoxyphenyl)amino]-1H-pyrrol-2(5H)-one
• 英文别名: 2-(4-chlorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2H-pyrrol-5-one
• CAS: 1075727-71-7
• 化学式: C₂₄H₂₁ClN₂O₃
• 分子量: 420.895
• InChiKey: UKIZRHMKAGCOSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  甲氧苯胺 在 1-butyl-1-methylpyrrolidinium hydrogen sulfate 作用下， 以 乙醇 为溶剂， 生成 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-[(4-methoxyphenyl)amino]-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

• A Convenient Method for the Preparation of 1,5-Diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones
  作者：Majid Ghashang、Yan-Song Zheng、Hamid Reza Shaterian

  DOI：10.1002/cjoc.201180323

  日期：2011.9

  A simple and eco‐friendly method for the preparation of 1,5‐diaryl‐3‐(arylamino)‐1H‐pyrrol‐2(5H)‐ones via the cyclo‐condensation reaction of aldehydes, amines and ethyl pyruvate in the presence of silica supported ferric chloride (SiO2‐FeCl3) as reusable heterogeneous catalyst is described. The present methodology offers several advantages such as excellent yields, simple procedure and short reaction

  通过醛，胺和丙酮酸乙酯在水中的醛，胺和丙酮酸乙酯的环缩合反应制备1,5-二芳基-3-（芳基氨基）-1 H-吡咯-2（5 H）-ones的一种简单而环保的方法。描述了存在二氧化硅负载的氯化铁（SiO 2 -FeCl 3）作为可重复使用的非均相催化剂。本方法提供了许多优点，例如优异的产率，简单的方法和较短的反应时间。
• Efficient One-Pot Synthesis of Substituted Lactams via Three-Component Solvent-Free Reaction Catalyzed by Ytterbium Triflate
  作者：Arasampattu S. Nagarajan、Boreddy S. R. Reddy

  DOI：10.1080/00397911.2011.628774

  日期：2013.5.3

  Abstract Three-component synthesis of 1,5-dihydro-2H-pyrrol-2-one derivatives from pyruvate, aldehyde, and aniline was described. The reaction proceeds successfully under solvent-free conditions using ytterbium as a catalyst. The structures of the synthesized compounds are assigned on the basis of elemental analysis, infrared, 1H NMR, 13C NMR, and mass spectral data. GRAPHICAL ABSTRACT

  摘要 描述了从丙酮酸、醛和苯胺三组分合成 1,5-二氢-2H-吡咯-2-酮衍生物。该反应在无溶剂条件下使用镱作为催化剂成功进行。根据元素分析、红外、1H NMR、13C NMR 和质谱数据确定合成化合物的结构。图形概要
• 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。