ethyl 2-methyl-1,4-diphenyl-1,4-dihydropyridine-3-carboxylate | 37875-78-8

• 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: ethyl 2-methyl-1,4-diphenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: 1,4-diphenyl-3-ethoxycarbonyl-2-methyl-1,4-dihydropyridine；2-methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester；ethyl 2-methyl-1,4-diphenyl-4H-pyridine-3-carboxylate
• CAS: 37875-78-8
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: WPODSHHYISCZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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 、 3-phenylaminobut-2-enoic acid ethyl ester 在 三氯化铁 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以93%的产率得到ethyl 2-methyl-1,4-diphenyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Lewis酸催化的顺序转换：功能性二氢吡啶的直接制备

  摘要：

  路易斯酸催化在温和的反应条件下，以高收率将β-烯胺丙烯酸酯或β-烯胺酮添加到α，β-不饱和醛中，从而生成取代的二氢吡啶。

  DOI：

  10.1002/adsc.200600343

文献信息

• Magnesium Perchlorate as Efficient Lewis Acid: A Simple and Convenient Route to 1,4-Dihydropyridines
  作者：Letizia Sambri、Giuseppe Bartoli、Krzysztof Babiuch、Marcella Bosco、Armando Carlone、Patrizia Galzerano、Paolo Melchiorre

  DOI：10.1055/s-2007-990839

  日期：——

  A new protocol for the synthesis of various 1,2,3,4-tetrasubstituted 1,4-dihydropyridines from enamino or carbonylic derivatives promoted by Mg(ClO4)2 is presented.

  本文提出了一种新的合成多种1,2,3,4-四取代-1,4-二氢吡啶的协议，该协议基于Mg(ClO4)2的促进作用，用于从烯胺或羰基衍生物进行合成。
• 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。
• A mild route for one pot synthesis of 5,6-unsubstituted 1,4-dihydropyridines catalyzed by sulphated mixed metal oxides
  作者：Sandeep S. Kahandal、Sandip R. Kale、Manoj B. Gawande、Radha V. Jayaram

  DOI：10.1039/c3cy00651d

  日期：——

  Synthesis of 1,4-dihydropyridines via a four component one pot reaction starting from α,β-unsaturated aldehyde, β-keto ester, amine and alcohol, catalysed by SO42−/CexZr1−xO2 is explored. The method has several advantages such as reusability of catalyst, avoidance of a multistep procedure and readily available starting materials. The protocol gives high to moderate yields for structurally diverse amines, β-keto esters and α,β-unsaturated aldehydes. SO42−/CexZr1−xO2 (x = 0.02–0.15 mol%) catalysts were prepared and characterized by various analytical techniques such as XRD, FT-IR, TGA-DSC, SEM-EDAX and the total acidity.

  探索了一种通过四组分一锅反应合成1,4-二氢吡啶的方法，反应起始物为α,β-不饱和醛、β-酮酯、胺和醇，催化剂为SO42−/CexZr1−xO2。该方法具有多个优点，如催化剂可重复使用、避免多步程序以及起始材料容易获得。该协议对结构多样的胺、β-酮酯和α,β-不饱和醛具有高至中等的产率。制备了SO42−/CexZr1−xO2（x = 0.02–0.15 mol%）催化剂，并通过多种分析技术如XRD、FT-IR、TGA-DSC、SEM-EDAX及总酸度进行表征。
• 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。
• Sulfonic Acid Functionalized Silica: An Efficient Heterogeneous Catalyst for a Three-Component Synthesis of 1,4-Dihydropyridines under Solvent-Free Conditions
  作者：Biswanath Das、Kanaparthy Suneel、Katta Venkateswarlu、Bommena Ravikanth

  DOI：10.1248/cpb.56.366

  日期：——

  Sulfonic acid functionalized silica catalyzed the three-component reaction of aromatic amines, alpha,beta-unsaturated aldehydes and beta-keto esters forming the corresponding 1,4-dihydropyridines in short reaction times and in high yields.

  磺酸官能化的二氧化硅以较短的反应时间和高收率催化了芳香胺，α，β-不饱和醛和β-酮酸酯的三组分反应，形成相应的1,4-二氢吡啶。