dimethyl 6-amino-5-cyano-1,4-diphenyl-1,4-dihydropyridine-2,3-dicarboxylate | 1420341-82-7

• 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-1,4-diphenyl-1,4-dihydropyridine-2,3-dicarboxylate
• 英文别名: dimethyl 6-amino-5-cyano-1,4-diphenyl-4H-pyridine-2,3-dicarboxylate
• CAS: 1420341-82-7
• 化学式: C₂₂H₁₉N₃O₄
• 分子量: 389.411
• InChiKey: FIRNLCZVOVRZOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 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：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲醛 、 苯胺 、 丁炔二酸二甲酯 、 丙二腈 在 potassium fluoride on basic alumina 作用下， 以 乙醇 为溶剂， 以80%的产率得到dimethyl 6-amino-5-cyano-1,4-diphenyl-1,4-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  KF / Al 2 O 3介导的多组分反应，可高效合成高度取代的二氢吡啶

  摘要：

  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。

  DOI：

  10.1002/jhet.1914

文献信息

• 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
• Synthesis of Dihydropyridine Derivatives under Eco‐friendly Approach and Investigation of Cytotoxic Activity
  作者：Avula Krishna Kumari、Vemulapati Hanuman Reddy、Guda Mallikarjuna Reddy、Yellala Venkata Rami Reddy、Suddala Leelavathi

  DOI：10.1002/jhet.3561

  日期：2019.5

  In an effort for development of innovative biologically active agents, a sequence of 1,4‐dihydropyridine analogues was synthesized through the green synthetic method. In addition, all compounds were evaluated for their cytotoxic activities against three human cancer cell lines and mouse melanoma and figured out the most active compounds. Besides, promoter reusability, easy handling of the chemical

  为了开发创新的生物活性剂，通过绿色合成方法合成了1,4-二氢吡啶类似物序列。此外，评估了所有化合物对三种人类癌细胞系和小鼠黑素瘤的细胞毒性活性，并找出了活性最高的化合物。此外，促进剂的可重复使用性，化学试剂的易处理性，简单的反应过程，最小化的时间，乙醇-水溶剂的相容性以及降低试剂的成本是实现这一卓有成效的途径的关键工具。因此，这些检查建议二氢吡啶及其衍生物是发现新的抗癌药物的动机部分。
• 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.
• Fe3O4@SiO2-NH2 Nanocomposite as a Robust and Effective Catalyst for the One-pot Synthesis of Polysubstituted Dihydropyridines
  作者：Mohammad Ali Ghasemzadeh、Mohammad Hossein Abdollahi-Basir

  DOI：10.17344/acsi.2016.2386

  日期：2016.9.15

  A practical, simple and efficient method for the synthesis of polysubstituted dihydropyridines was described via multicomponent reactions of aldehydes, arylamines, dimethyl acetylenedicarboxylate and malononitrile/ ethyl acetoacetate in the presence of Fe3O4@SiO2-NH2 nanocomposites. The present methodology provides a novel and efficient method for the synthesis of dihydropyridine derivatives with some advantages, such as excellent yields, short reaction times, recoverability and low catalyst loading. The nanomagnetic catalyst could be readily recovered using an external magnet and reused several times without any significant loss in activity. The catalyst was fully characterized by FT-IR, SEM, XRD, EDX and VSM analysis.