methyl 4-(cyclohexylamino)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate | 1173196-86-5

• 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-(cyclohexylamino)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: methyl 4-(cyclohexylamino)-5-oxo-1-phenyl-2H-pyrrole-3-carboxylate
• CAS: 1173196-86-5
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: YMDAPLQRDOZWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  聚合甲醛 、 环己胺 、 苯胺 、 丁炔二酸二甲酯 在 Co₂FeO₄ coated silica deposited on isoreticular metal organic framework 作用下， 以 甲醇 、 水 为溶剂， 反应 1.83h， 以90%的产率得到methyl 4-(cyclohexylamino)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  磁性金属-有机骨架 CoFe2O4@SiO2@IRMOF-3 作为一锅法合成功能化二氢-2-氧代吡咯的高效催化剂

  摘要：

  一种基于磁性金属-有机骨架的催化剂 CoFe 2 O 4 @SiO 2 @IRMOF-3 被制备并鉴定为一种有效的催化剂，用于通过一锅四组分合成各种功能化的二氢-2-氧代吡咯乙炔二羧酸二烷基酯、芳胺、甲醛和任选的第二胺或二胺在室温下的反应。即使经过八次反应循环后，该催化剂也能被磁性分离和回收，其催化效率没有显着损失。

  DOI：

  10.1055/s-0036-1588924

文献信息

• Nano Fe3O4 as a magnetically recyclable, powerful, and stable catalyst for the multi-component synthesis of highly functionalized dihydro-2-oxopyrroles
  作者：Mohammad Nickraftar、Nahid Najafi Hajivar、Jasem Aboonajmi、Elham Fereidooni

  DOI：10.1007/s11164-015-2185-0

  日期：2016.4

  Abstract A mild and efficient method for the one-pot synthesis of functionalized dihydro-2-oxopyrroles is described via four-component domino reaction of amines, dialkyl acetylenedicarboxylates, and formaldehyde in the presence of super magnetic nano iron oxide (nano Fe3O4) in EtOH at room temperature. The major advantages of the present method are mild and green reaction conditions, high yields, short

  摘要 在超磁性纳米氧化铁（纳米Fe 3 O 4）存在下，通过胺，乙炔基二羧酸二烷基酯和甲醛的四组分多米诺反应，描述了一种温和高效的一锅合成官能化二氢-2-氧吡咯的方法。在室温下在乙醇中。本方法的主要优点是温和绿色反应条件，高收率，较短的反应时间，清洁的反应，可磁循环使用的催化剂，原子经济性（63-76％），操作简便且无需柱色谱法。发现该催化剂是可回收的并且可以使用多达六次而不会显着降低其活性。 图形概要
• A novel class of small-molecule caspase-3 inhibitors prepared by multicomponent reactions
  作者：Qiuhua Zhu、Lixin Gao、Zhipeng Chen、Sichao Zheng、Huafei Shu、Jia Li、Huanfeng Jiang、Shuwen Liu

  DOI：10.1016/j.ejmech.2012.05.001

  日期：2012.8

  A series of tetra- and pentasubstituted polyfunctional dihydropyrroles 5 and 6 were synthesized via practical multicomponent reactions (MCRs) for research on their structure activity relationship as caspase-3 inhibitors. Among 39 compounds evaluated, 14 of them exhibited inhibition against caspase-3 with IC50 ranging from 5 to 20 mu M. The inhibitory activities of 5 and 6 depend on the nature of substituents on different positions. 5 and 6 possess a different scaffold from those previously reported and are the first caspase-3 inhibitors prepared via MCRs. The most active compounds 5k (IC50 = 5.27 mu M) could therefore be used as a lead for the development of highly potent caspase-3 inhibitors as drug candidates for therapeutic agents by taking advantage of MCRs. (C) 2012 Elsevier Masson SAS. All rights reserved.
• One-pot four-component domino reaction for the synthesis of substituted dihydro-2-oxypyrrole catalyzed by molecular iodine
  作者：Abu T. Khan、Arindam Ghosh、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2012.03.046

  日期：2012.5

  The synthesis of multi-functionalized dihydro-2-oxypyrrole can be achieved using one-pot four-component domino reaction from dialkylacetylene dicarboxylate, amines, and formaldehyde by employing molecular iodine as catalyst at room temperature. The salient features of the present method are: simple, straightforward, cost-effective, environmentally benign, and no column chromatographic separation is applicable on a broad range of substrates. (C) 2012 Elsevier Ltd. All rights reserved.
• Magnetic Metal–Organic Framework CoFe2O4@SiO2@IRMOF-3 as an Efficient Catalyst for One-Pot Synthesis of Functionalized Dihydro-2-oxopyrroles
  作者：Zhan-Hui Zhang、Jia-Nan Zhang、Xiu-Huan Yang、Wei-Jie Guo、Bo Wang

  DOI：10.1055/s-0036-1588924

  日期：——

  metal–organic framework-based catalyst CoFe 2 O 4 @SiO 2 @IRMOF-3 was prepared and identified as an efficient catalyst for the synthesis of a variety of functionalized dihydro-2-oxopyrroles by a one-pot, four-component reaction of a dialkyl acetylenedicarboxylate, an aryl amine, formaldehyde, and optionally a second amine or diamine at room temperature. The catalyst was magnetically separated and recovered

  一种基于磁性金属-有机骨架的催化剂 CoFe 2 O 4 @SiO 2 @IRMOF-3 被制备并鉴定为一种有效的催化剂，用于通过一锅四组分合成各种功能化的二氢-2-氧代吡咯乙炔二羧酸二烷基酯、芳胺、甲醛和任选的第二胺或二胺在室温下的反应。即使经过八次反应循环后，该催化剂也能被磁性分离和回收，其催化效率没有显着损失。