dimethyl 6-amino-5-cyano-4-(3-nitrophenyl)-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate | 1420342-31-9

• 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: dimethyl 6-amino-5-cyano-4-(3-nitrophenyl)-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate
• 英文别名: dimethyl 6-amino-5-cyano-4-(3-nitrophenyl)-1-phenyl-4H-pyridine-2,3-dicarboxylate
• CAS: 1420342-31-9
• 化学式: C₂₂H₁₈N₄O₆
• 分子量: 434.408
• InChiKey: JVZUHMFCVBFZOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 苯胺 、 丁炔二酸二甲酯 、 丙二腈 以 水 为溶剂， 反应 4.0h， 以93%的产率得到dimethyl 6-amino-5-cyano-4-(3-nitrophenyl)-1-phenyl-1,4-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Visible Light Mediated, Catalyst Free, One-Pot Convenient Synthesis of Dihydropyridines

  摘要：

  一种简单、高效、环保的方法已经被开发出来，用于通过一锅法四组分反应合成多取代二氢吡啶。该反应在室温下，在无催化剂的情况下，在水乙酸乙酯溶液中受到可见光照射。该方法的主要优点是反应条件温和，产率高，无需柱层析，反应过程干净，从经济角度来看环保可持续。

  DOI：

  10.2174/1570178618666210125162342

文献信息

• Improved One-Pot, Four-Component Strategy to Access ­Functionalized Dihydropyridines by Using 4-(N,N-Dimethylamino)pyridine as a Catalyst
  作者：Appaswami Lalitha、Rathinam Ramesh、Mani Arivazhagan、Jan Malecki

  DOI：10.1055/s-0037-1609579

  日期：2018.9

  strategy has been developed for the synthesis of structurally diverse novel 1,4-dihydropyridine frameworks bearing a 3-nitrophenyl moiety through a one-pot, four-component reaction with 4-(N,N-dimethylamino)pyridine as a catalyst at room temperature. This tandem process proceeds more effectively than previous catalytic processes.

  已经开发了一种方便的策略，用于通过与 4-(N,N-二甲氨基)吡啶作为催化剂的一锅四组分反应合成具有 3-硝基苯基部分的结构多样的新型 1,4-二氢吡啶骨架。室内温度。这种串联过程比以前的催化过程更有效。
• 3,6-Dioxaoctamethylenediamminium trifluoromethanesulfonate [3,6-DOMDA]OTf as a novel ionic liquid catalyst for the synthesis of functionalized 1,4-dihydropyridines
  作者：Saeed Baghery、Mohammad Ali Zolfigol

  DOI：10.1016/j.molliq.2017.02.073

  日期：2017.4

  as a novel ionic liquid was synthesized and fully characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (1H NMR, 13C NMR, 19F NMR), Mass spectrometry, Thermal gravimetric (TG), Derivative thermal gravimetric (DTG) and Differential thermal analysis (DTA). Described [3,6-DOMDA]OTf was used as a novel ionic liquid catalyst for the domino one-pot four-component synthesis of functionalized

  在这项研究中，合成了[3,6-DOMDA] OTf作为新型离子液体，并通过傅里叶变换红外（FT-IR），核磁共振（1 H NMR，13 C NMR，19F NMR），质谱，热重（TG），微分热重（DTG）和差热分析（​​DTA）。描述的[3,6-DOMDA] OTf用作新型离子液体催化剂，用于在溶剂中，由多种醛，丙二腈，乙炔二羧酸酯和苯胺的组合，用于多官能团的多米诺骨牌四锅合成功能化1,4-二氢吡啶衍生物。在50°C下处于自由状态。具有醚键的[3,6-DOMDA] OTf催化剂可以回收并重复使用多达六次，而不会显着降低活性。所提及的化合物以高至优异的产率，短的反应时间合成并且其产物可以容易地分离。
• 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。
• 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.