2-methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester | 1021949-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 2-methyl-1,4-diphenyl-4H-pyridine-3-carboxylate
• CAS: 1021949-61-0
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: DWYYDKOEDVBPGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 乙酰乙酸甲酯 、 苯胺 在 L-脯氨酸 作用下， 反应 1.0h， 以89%的产率得到2-methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Organocatalysed three-component domino synthesis of 1,4-dihydropyridines under solvent free conditions

  摘要：

  An organocatalysed protocol for one-pot synthesis of 1,4-dihydropyridines via three-component coupling of cinnamaldehyde, aniline and beta-keto esters under solvent free conditions at ambient temperature is reported. The reaction is generally very fast and the products are obtained in high yield. The catalytic activity of small organic molecules like amino acids (acidic, basic and neutral), ephedrine and cinchona alkaloids was studied. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.022

文献信息

• Synthesis and biological evaluation of N-aryl-1,4-dihydropyridines as novel antidyslipidemic and antioxidant agents
  作者：Atul Kumar、Ram Awatar Maurya、Siddharth Sharma、Mukesh Kumar、Gitika Bhatia

  DOI：10.1016/j.ejmech.2009.10.036

  日期：2010.2

  cinnamaldehydes, anilines and 2-keto esters in methanol. The synthesized compounds were screened for their antidyslipidemic and antioxidant activity in vivo and in vitro. Compounds 2a, 2g, and 2l have exhibited promising lipid and TG lowering activity, whereas compounds 2m and 2n have showed potent antioxidant activity.

  N-芳基-1,4-二氢吡啶2a - n是通过碘催化肉桂醛，苯胺和2-酮酯在甲醇中的三组分反应合成的。筛选合成的化合物在体内和体外的抗血脂异常和抗氧化活性。化合物2a，2g和2l显示出有希望的脂质和TG降低活性，而化合物2m和2n显示出有效的抗氧化活性。
• An Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic Nanocrystalline Fe₃O₄
  作者：Shu-Hong Yang、Fei-Yang Zhao、Hong-Yan Lü、Jia Deng、Zhan-Hui Zhang

  DOI：10.1002/jhet.953

  日期：2012.9

  An efficient approach for one‐pot three‐component reaction of aromatic amines, α,β‐unsaturated aldehydes and β‐keto esters using magnetic nanocrystalline Fe3O4 as a catalyst has been described. The corresponding 1,4‐dihydropyridines are obtained in good yields under mild conditions. In addition, the catalyst can be recovered with a magnet and reused at least five consecutive cycles without appreciable

  描述了一种使用磁性纳米晶体Fe 3 O 4作为催化剂进行芳族胺，α，β-不饱和醛和β-酮酸酯的单锅三组分反应的有效方法。在温和的条件下，可以良好的收率获得相应的1,4-二氢吡啶。此外，可以用磁体回收催化剂，并至少连续五个循环重复使用，而不会明显降低其催化活性。
• Silica-supported Perchloric Acid Catalyzed One-pot Synthesis of 1,4-Dihydropyridines
  作者：Dasari Ramesh、Singanaboina Rajaram、Manchala Narasimhulu、Thummalpally Srikanth Reddy、Kondempudi Chinni Mahesh、Gajji Manasa、Yenamandra Venkateswarlu

  DOI：10.1002/cjoc.201100032

  日期：2011.11

  AbstractAn environmentally friendly and highly efficient procedure for the preparation of 1,4‐dihydropyridines by the reaction between α,β‐unsaturated aldehydes, aromatic amines and β‐keto esters in the presence of silica supported perchloric acid is described.
• Organocatalysed three-component domino synthesis of 1,4-dihydropyridines under solvent free conditions
  作者：Atul Kumar、Ram Awatar Maurya

  DOI：10.1016/j.tet.2008.02.022

  日期：2008.4

  An organocatalysed protocol for one-pot synthesis of 1,4-dihydropyridines via three-component coupling of cinnamaldehyde, aniline and beta-keto esters under solvent free conditions at ambient temperature is reported. The reaction is generally very fast and the products are obtained in high yield. The catalytic activity of small organic molecules like amino acids (acidic, basic and neutral), ephedrine and cinchona alkaloids was studied. (c) 2008 Elsevier Ltd. All rights reserved.