5-ethyl 2,3-dimethyl 6-amino-1-(4-chlorophenyl)-1,4-dihydro-4-(3-nitrophenyl)pyridine-2,3,5-tricarboxylate | 1239897-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-ethyl 2,3-dimethyl 6-amino-1-(4-chlorophenyl)-1,4-dihydro-4-(3-nitrophenyl)pyridine-2,3,5-tricarboxylate
• 英文别名: 5-ethyl 2,3-dimethyl 6-amino-1-(4-chlorophenyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-2,3,5-tricarboxylate；5-O-ethyl 2-O,3-O-dimethyl 6-amino-1-(4-chlorophenyl)-4-(3-nitrophenyl)-4H-pyridine-2,3,5-tricarboxylate
• CAS: 1239897-56-3
• 化学式: C₂₄H₂₂ClN₃O₈
• 分子量: 515.907
• InChiKey: KZEHTIGJNLVBQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-氰基-3-(3-硝基苯基)丙烯酸乙酯 、 对氯苯胺 、 丁炔二酸二甲酯 以 乙醇 为溶剂， 反应 10.0h， 生成 5-ethyl 2,3-dimethyl 6-amino-1-(4-chlorophenyl)-1,4-dihydro-4-(3-nitrophenyl)pyridine-2,3,5-tricarboxylate
  参考文献：
  名称：

  芳香醛，丙二腈，芳胺和乙二酸二羧酸酯的四组分反应合成多取代的二氢吡啶

  摘要：

  在三乙胺作为碱助催化剂的存在下，通过芳族醛，丙二腈，芳基胺和乙炔二羧酸酯在乙醇中的独特的四组分反应，开发了一种制备多取代的二氢吡啶的实用有效的方法。该四组分反应是原子有效的，高产率的，并且适用于各种各样的四组分反应。

  DOI：

  10.1021/ol101475b

文献信息

• One-Pot Multicomponent Reactions for the Efficient Synthesis of Highly Functionalized Dihydropyridines
  作者：Suman Pal、Lokman H. Choudhury、Tasneem Parvin

  DOI：10.1080/00397911.2011.618283

  日期：2013.3.1

  atom-economic, one-pot protocol has been developed for the synthesis of highly functionalized dihydropyridines via four-component reactions of aromatic aldehydes, arylamines, malononitrile, and dimethylacetylenedicarboxylate in the presence of sodium hydroxide in ethanol. This domino reaction proceeded smoothly in good to excellent yields and offered several advantages, including short reaction time, simple

  摘要 已开发出一种高效、原子经济、一锅法的方案，用于在乙醇中存在氢氧化钠的情况下，通过芳香醛、芳胺、丙二腈和二甲基乙炔二甲酸酯的四组分反应合成高度官能化的二氢吡啶。这种多米诺反应以良好的收率顺利进行，并提供了几个优点，包括反应时间短、实验程序简单以及适用于广泛的底物。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• KF/Al₂O₃Mediated Multicomponent Reactions for the Efficient Synthesis of Highly Substituted Dihydropyridines
  作者：Suman Pal、Md. Nasim Khan、Lokman H. Choudhury

  DOI：10.1002/jhet.1914

  日期：2014.8

  KF/Al2O3 was found to be an efficient solid supported catalyst for the facile access of highly substituted dihydropyridine derivatives from the multicomponent reaction of aromatic aldehydes, amines, malononitrile, and alkylacetylenedicarboxylates. The notable advantages of this protocol are reusable catalyst, good yields, applicable to a wide range of substrates for the synthesis of pharmacologically interesting

  KF / Al的2 ö 3被认为是用于从高度取代的二氢吡啶衍生物的容易访问一个有效的固体负载型催化剂的多组分反应的芳族醛，胺的，丙二腈和烷基乙炔二羧酸盐。该方案的显着优势是可重复使用的催化剂，良好的收率，适用于合成药理学上令人感兴趣的二氢吡啶衍生物的各种底物。
• A comparative study of the catalytic activity of nanosized oxides in the one-pot synthesis of highly substituted dihydropyridines
  作者：Javad Safaei-Ghomi、Elham Heidari-Baghbahadorani、Hossein Shahbazi-Alavi、Mehrnoosh Asgari-Kheirabadi

  DOI：10.1039/c4ra14557g

  日期：——

  A four-component reaction of aromatic aldehydes, ethyl cyanoacetate, arylamines, and dimethyl acetylenedicarboxylate has been achieved in the presence of nanosized oxides (ZnO NPs, CuO NPs, CeO2 NPs, SnO NPs, MgO NPs and CaO NPs) as highly effective heterogeneous catalysts to produce polysubstituted dihydropyridines. Extraordinarily, the best results were obtained using CeO2 nanoparticles as an efficient

  在纳米氧化物（ZnO NP，CuO NP，CeO 2 NP，SnO NP，MgO NP和CaO NP）存在下，芳族醛，氰基乙酸乙酯，芳基胺和乙酰二甲酸二甲酯的四组分反应已经实现。生产多取代的二氢吡啶的催化剂。特别地，使用CeO 2纳米颗粒作为有效催化剂获得了最佳结果。该方法具有几个优点，包括温和的反应条件，适用于广泛的底物，催化剂的可重复使用性和最小的催化剂负载量。
• PEG-mediated one-pot multicomponent reactions for the efficient synthesis of functionalized dihydropyridines and their functional group dependent DNA cleavage activity
  作者：Suman Pal、Vandana Singh、Prolay Das、Lokman H. Choudhury

  DOI：10.1016/j.bioorg.2013.03.003

  日期：2013.6

  Polyethylene glycol (PEG) has been found to be an inexpensive, non-toxic and useful medium for the one pot synthesis of highly functionalized dihydropyridines using multicomponent reactions (MCRs) at room temperature under catalyst free conditions. The notable features of this protocol are: mild reaction condition, applicability to wide range of substrates, reusability of the PEG and good yields. The interaction of the synthesized compounds with pUC19 plasmid DNA was also analyzed. Some of the synthesized compounds showed interesting functional group dependent nuclease activity for plasmid DNA cleavage under physiological conditions. (C) 2013 Elsevier Inc. All rights reserved.
• Synthesis of Polysubstituted Dihydropyridines by Four-Component Reactions of Aromatic Aldehydes, Malononitrile, Arylamines, and Acetylenedicarboxylate
  作者：Jing Sun、Er-Yan Xia、Qun Wu、Chao-Guo Yan

  DOI：10.1021/ol101475b

  日期：2010.8.20

  procedure for the preparation of the polysubstituted dihydropyridines was developed through a unique four-component reaction of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate in ethanol in the presence of triethylamine as a base promoter. This four-component reaction is atom-efficient, high-yielding, and applicable to a wide variety of four-component reactions.

  在三乙胺作为碱助催化剂的存在下，通过芳族醛，丙二腈，芳基胺和乙炔二羧酸酯在乙醇中的独特的四组分反应，开发了一种制备多取代的二氢吡啶的实用有效的方法。该四组分反应是原子有效的，高产率的，并且适用于各种各样的四组分反应。