diethyl 4-(2-phenylethenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate | 1539-43-1

• 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: diethyl 4-(2-phenylethenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate
• 英文别名: Diethyl 2,6-dimethyl-4-(4-styryl)pyridine-3,5-dicarboxylate；diethyl 1,6-dimethyl-4-cinnamylpyridine-3,5-dicarboxylate；diethyl 2,6-dimethyl-4-styrylpyridine-3,5-dicarboxylate；2,6-dimethyl-4-styryl-pyridine-3,5-dicarboxylic acid diethyl ester；2,6-Dimethyl-4-styryl-pyridin-3,5-dicarbonsaeure-diaethylester；Diethyl 2,6-dimethyl-4-(2-phenylethenyl)pyridine-3,5-dicarboxylate
• CAS: 1539-43-1
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: JJJYFEJNOXLMRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diethyl 1,4-dihydro-2,6-dimethyl-4-[(E)-2-phenylethenyl]pyridine-3,5-dicarboxylate 在 1-丁基-3-甲基咪唑溴盐 、 二苯二硫醚 作用下， 反应 1.5h， 以80%的产率得到diethyl 4-(2-phenylethenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Biomimetic Aromatization of Hantzsch 1,4-Dihydropyridines by S-S Bonds under Mild Conditions

  摘要：

  For the first time Hantzsch 1,4-dihydropyridines were oxidized to the corresponding pyridines by diphenyl disulfide in ionic liquid.

  DOI：

  10.3987/com-07-11030

文献信息

• CAN Mediated Mechanochemical Synthesis of Substituted Pyridine Derivatives
  作者：Radhika Khanna、Aarti Dalal、Kulbir Kadyan、Ramesh Kumar、Parvin Kumar、Ramesh C. Kamboj

  DOI：10.2174/1570178615666180102153707

  日期：2018.7.2

  A simple, green and cost-effective protocol has been devised for the synthesis of 4-substituted-2,6-dimethyl-3,5-pyridinecarboxylates from Hantzsch-type 1,4-dihydropyridines via rapid oxidation in excellent yields using 1.5 equivalent of ceric ammonium nitrate within 15 minutes in solvent-free conditions. The method was able to furnish the products in excellent yields. The products obtained were characterized by their NMR and melting points data.

  一种简便、绿色且经济的合成方法已被设计出来，用于从汉奇型1,4-二氢吡啶通过快速氧化合成4-取代-2,6-二甲基-3,5-吡啶羧酸盐，使用1.5当量的硝酸铈铵在无溶剂条件下15分钟内实现优异的产率。该方法能够以优异的产率提供产物。所得产物通过其核磁共振和熔点数据进行表征。
• Facile Aromatisation of Hantzsch 1,4-Dihydropyridines by Autoxidation in the Presence of <i>P</i>-toluenesulfonic Acid in Acetic Acid
  作者：Ding Zhang、Min Sha

  DOI：10.3184/174751918x15208600846791

  日期：2018.3

  A simple protocol to achieve the aromatisation of Hantzsch dihydropyridines in high yield was established using p-toluenesulfonic acid in acetic acid and yields of 90% were obtained at room temperature. With regards to the Hantzsch 1,4-dihydropyridines derived from alkyl aldehydes bearing one or more á-hydrogens, dealkylation products were obtained through a proposed autoxidation mechanism.

  使用乙酸中的对甲苯磺酸建立了以高产率实现 Hantzsch 二氢吡啶芳构化的简单方案，并且在室温下获得了 90% 的产率。对于衍生自带有一个或多个 α-氢的烷基醛的 Hantzsch 1,4-二氢吡啶，通过提出的自氧化机制获得了脱烷基产物。
• Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines
  作者：Parvin Kumar、Kulbir Kadyan、Meenakshi Duhan、Jayant Sindhu、Khalid Hussain、Sohan Lal

  DOI：10.1007/s11696-018-0666-5

  日期：2019.5

  An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising

  开发了一种有效和环境友好的方法，用于将1，4-二氢吡啶氧化成相应的吡啶衍生物。使用二氧化硅负载的硝酸铈铈铵作为催化剂在CH 3 CN中进行室温或不超声处理，探索了1,4-二氢吡啶的氧化芳构化作用。这种负载型催化剂起着更有效的氧化剂的作用，并且在反应时间和收率方面都比其他报道的试剂更具优势。与不支持的形式相比，发现支持的试剂更有效和更具选择性。在本反应中未观察到Belousov–Zhabotinskii反应。在4-正烷基/ n情况下观察到的脱烷基在当前情况下也未观察到-烯基与其他氧化剂的结合。
• An Expeditious Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Cetyltrimethylammonium Peroxodisulfate: A Phase Transferring Oxidant
  作者：Parvin Kumar、Ashwani Kumar

  DOI：10.5012/bkcs.2010.31.8.2299

  日期：2010.8.20

  A new approach to the use of potassium peroxodisulphate as an oxidizing reagent is proposed and applied to the case of oxidative aromatization of 1, 4-dihydropyridines with cetyltrimethylammonium peroxodisulfate, a phase transfer oxidant. We demonstrate how it is possible to increase the reactivity of potassium peroxodisulphate in the presence of phase transfer catalyst. Dealkylation in case of 4-n-alkyl/n-alkenyl

  提出了一种使用过二硫酸钾作为氧化剂的新方法，并将其应用于相转移氧化剂十六烷基三甲基过二硫酸铵对 1, 4-二氢吡啶的氧化芳构化。我们展示了在相转移催化剂存在下如何提高过二硫酸钾的反应性。在 4-n-烷基/n-烯基的情况下没有获得脱烷基化。
• Aromatization of Hantzsch 1,4-Dihydropyridines with Urea-Hydrogen Peroxide/Maleic Anhydride
  作者：Ahmad R. Momeni、Hamid Aliyan、Heidar Mombeini、Ahmad R. Massah、Hamid J. Naghash

  DOI：10.1515/znb-2006-0314

  日期：2006.3.1

  A simple method for the oxidative aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridines is reported using urea-hydrogen peroxide/maleic anhydride in acetonitrile.

  报道了一种简单的方法，利用乙腈中的尿素-过氧化氢/马来酸酐，将Hantzsch 1,4-二氢吡啶氧化芳香化为相应的吡啶。