ethyl 1-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate | 37875-83-5

• 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 1-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: 1-p-chlorophenyl-3-ethoxycarbonyl-2-methyl-4-phenyl-1,4-dihydropyridine；1-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylic acid ethyl ester；ethyl 2-methyl-1-(4-chlorophenyl)-4-phenyl-1,4-dihydropyridine-3-carboxylate；ethyl 1-(4-chlorophenyl)-2-methyl-4-phenyl-4H-pyridine-3-carboxylate
• CAS: 37875-83-5
• 化学式: C₂₁H₂₀ClNO₂
• 分子量: 353.848
• InChiKey: LACDEMZVQFKJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 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：

  2,3-丁二烯酸乙酯 、 N-(4-chlorophenyl)-3-phenylprop-2-en-1-imine 以 苯 为溶剂， 反应 55.0h， 以94%的产率得到ethyl 1-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  简便的区域选择性[4 + 2]环加成反应，涉及1-芳基-4-苯基-1-氮杂二烯和烯丙酸酯：制备新型取代的1-芳基-4-苯基-1,4-二氢吡啶的有效途径。

  摘要：

  [反应：请参阅文本] 1-芳基-4-苯基-1-氮杂二烯在回流的苯中的烯丙酯的C2，C3π键上进行容易的区域选择性[4 + 2]环加成，生成的加合物经历1， 3-H转变得到新颖的2-烷基-1-芳基-3-乙氧基羰基-4-苯基-1,4-二氢吡啶（78-97％）。然而，当反应在室温下进行时，除了[4 + 2]加成以外，还涉及[2 + 2]的加成方式，涉及氮杂二烯的C ＝ N和烯丙酸酯的C 3，C 4π键。所得的N-芳基-2-乙氧基-羰基-亚甲基-4-苯乙烯基氮杂环丁烷（17-28％）在硅胶上进行重组，得到2-环己烯-1-酮。

  DOI：

  10.1021/ol010026a

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。
• 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。
• A new three-component domino synthesis of 1,4-dihydropyridines
  作者：Vellaisamy Sridharan、Paramasivan T. Perumal、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1016/j.tet.2007.03.092

  日期：2007.5

  three-component domino reaction between aromatic amines, α,β-unsaturated aldehydes, and ethyl acetoacetate, providing an efficient new entry into 1,4-dihydropyridines. This new reaction requires very mild reaction conditions, has water as the only side product and is complementary to the classical Hantzsch synthesis in that it is well suited to the preparation of N-aryl-5,6-unsubstituted dihydropyridines. Experiments

  硝酸铈铵（CAN）催化芳族胺，α，β-不饱和醛与乙酰乙酸乙酯之间的三组分多米诺反应，为1,4-二氢吡啶提供了一种有效的新途径。该新反应需要非常温和的反应条件，水是唯一的副产物，并且与经典的汉茨化学合成法互补，因为它非常适合于制备N-芳基-5,6-未取代的二氢吡啶。在存在自由基陷阱的情况下进行的实验表明，可以排除单电子氧化机理，并且CAN可以充当路易斯酸。