methyl 4-(benzylamino)-1-(4-chlorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | 1374118-86-1

• 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: methyl 4-(benzylamino)-1-(4-chlorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: methyl 4-(benzylamino)-1-(4-chlorophenyl)-5-oxo-2H-pyrrole-3-carboxylate
• CAS: 1374118-86-1
• 化学式: C₁₉H₁₇ClN₂O₃
• 分子量: 356.809
• InChiKey: JSTZNQBFXNBRKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苄胺 在 草酸 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 methyl 4-(benzylamino)-1-(4-chlorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A One-pot Multi-component Synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates Catalysed by Oxalic Acid Dihydrate

  摘要：

  本发明介绍了在甲醇中以草酸二水合物（20 摩尔%）为催化剂，通过胺、乙炔二甲酸二烷基酯和甲醛的单锅多组分反应，简单合成 N-芳基-3-氨基二氢吡咯-2-酮-4-羧酸酯的方法。这种均相催化过程具有反应条件温和、产率高、反应时间短、起始原料简单易得、易于操作以及无需柱层析等优点。

  DOI：

  10.3184/174751912x13547952669204

文献信息

• Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Adel Beigbabaei、Anthony C. Willis

  DOI：10.1007/s13738-013-0222-8

  日期：2013.10

  Extremely facile and efficient procedures have been developed for the synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles via one-pot multi-component reactions in the presence of Al(H2PO4)3 as a heterogeneous and eco-friendly catalyst under mild conditions. The multi-component reaction of aromatic aldehydes, aromatic amines, and β-keto esters catalyzed by Al(H2PO4)3 in EtOH at room

  在Al（H 2 PO 4）3作为非均相和生态友好型催化剂的存在下，通过单锅多组分反应合成高度官能化的哌啶和二氢-2-氧基吡咯的方法极为简便有效。温和的条件。Al（H 2 PO 4）3催化的芳香醛，芳香胺和β-酮酯的多组分反应在室温下，在乙醇中提供高官能度的哌啶，收率良好至极佳。这些功能化的哌啶的结构和相对立体化学通过单X射线晶体学分析证实。发现相同的催化剂可用于在环境温度下使用胺，乙炔二羧酸二烷基酯和甲醛在甲醇中的四组分反应来合成多官能化的二氢-2-氧基吡咯。发现该催化剂是可回收的，并且可以使用多达五次而不会显着降低其活性。
• TRIFLUOROACETIC ACID CATALYZED ONE-POT FOUR-COMPONENT DOMINO REACTION FOR THE SYNTHESIS OF SUBSTITUTED DIHYDRO 2-OXYPYRROLES
  作者：Mojtaba Lashkari、Malek Taher Maghsoodlou、Mahsa Karima、Mehrnoosh Kangani

  DOI：10.4067/s0717-97072018000103799

  日期：——

  Trifluoroacetic acid was applied as an efficient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temperature in methanol. This methodology includes number of advantages such as: short reaction time, clean work-up, use of inexpensive catalyst, high

  三氟乙酸是在环境温度下通过胺，甲醛和乙酰二羧酸二烷基酯的多米诺反应，作为一种有效的催化剂，用于一锅四组分合成N-芳基/烷基-3-氨基二氢吡咯-2-酮-4-羧酸酯。甲醇。该方法包括许多优点，例如：反应时间短，清洁后处理，使用廉价的催化剂，高收率和清洁后处理。该反应的后处理仅涉及过滤和用MeOH的简单洗涤步骤，并且不需要柱色谱法。
• Coupling of amines, dialkyl acetylenedicarboxylates and formaldehyde promoted by [n-Bu4N][HSO4]: an efficient synthesis of highly functionalized dihydro-2-oxopyrroles and bis-dihydro-2-oxopyrroles
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri

  DOI：10.1007/s11164-012-0998-7

  日期：2014.2

  Abstract Tetrabutylammonium hydrogen sulfate [ n -Bu4N][HSO4] is used as an efficient catalyst for the one-pot, multi-component synthesis of highly substituted dihydro-2-oxopyrroles and bis-dihydro-2-oxopyrroles by means of reaction between amines, dialkyl acetylenedicarboxylates and formaldehyde in methanol at ambient temperature. This homogeneous catalyst procedure includes some important aspects

  摘要 硫酸四丁基铵硫酸氢钠[ n -Bu 4 N] [HSO 4 ]是一种高效催化剂，可通过一锅法，多组分合成高取代度的二氢-2-氧代吡咯和双二氢-2-氧代吡咯。室温下，胺，乙炔二羧酸二烷基酯和甲醛之间的反应 这种均相催化剂程序包括一些重要方面，例如易于后处理，无需柱色谱，简单易用的前体，相对短的反应时间和高收率。 图形概要
• ZrCl4 as an efficient catalyst for one-pot four-component synthesis of polysubstituted dihydropyrrol-2-ones
  作者：Seyed Sajad Sajadikhah、Malek Taher Maghsoodlou、Nourallah Hazeri、Sajad Mohamadian-Souri

  DOI：10.1007/s11164-015-2178-z

  日期：2016.4

  Abstract An efficient synthesis of polysubstituted dihydropyrrol-2-one derivatives via one-pot four-component domino reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of zirconium tetrachloride (ZrCl4) is described. The presented methodology offers several advantages such as simplicity of operation, good to high yields, short reaction times, inexpensive and readily

  摘要 描述了在四氯化锆（ZrCl 4）存在下，通过胺，乙炔二羧酸二烷基酯和甲醛的一锅四组分多米诺反应有效合成多取代的二氢吡咯-2-酮衍生物。所提出的方法具有许多优点，例如操作简单，产率高至高，反应时间短，廉价和容易获得的起始原料和催化剂。此外，产物通过简单的过滤而获得，无需柱色谱法。 图形概要
• 8-Hydroxyquinoline Functionalized PEG-1000 Bridged Dicationic Ionic Liquid as a Novel Ligand for Copper-catalyzed<i>N</i>-Arylation of Imidazoles
  作者：Ying-Lei Wang、Jun Luo、Zu-Liang Liu

  DOI：10.1002/jccs.201300008

  日期：2013.8

  A novel 8‐hydroxyquinoline functionalized PEG‐1000 bridged dicationic ionic liquid ([HQ‐PEG1000‐DIL][BF4]) was synthesized and characterized. It was applied as an efficiently recyclable ligand for copper‐catalyzed N‐arylation of nitrogen‐containing heterocycles with aryl halides. The catalytic system could be easily recovered and reused for at least five runs without obvious loss of catalytic activity

  合成并表征了新型的8-羟基喹啉官能化PEG-1000桥接的双离子液体（[HQ-PEG 1000 - DIL] [BF 4 ]）。它被用作含氮杂环与芳基卤化物的铜催化N芳基化反应的有效可循环配体。该催化体系可以很容易地回收并重复使用至少五次，而不会明显丧失催化活性。