diethyl 2,6-dimethyl-4-(2-chlorophenyl)-3,5-pyridinedicarboxylate | 94384-12-0

• 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: diethyl 2,6-dimethyl-4-(2-chlorophenyl)-3,5-pyridinedicarboxylate
• 英文别名: diethyl 4-(2-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate；4-(2-Chlor-phenyl)-2,6-dimethyl-3,5-bis-ethoxycarbonyl-pyridin；4-(2-chloro-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester；4-(2-Chlor-phenyl)-2,6-dimethyl-pyridin-3,5-dicarbonsaeure-diaethylester；Diethyl 4-(2-chlorophenyl)-2,6-dimethyl-3,5-pyridine-dicarboxylate
• CAS: 94384-12-0
• 化学式: C₁₉H₂₀ClNO₄
• 分子量: 361.825
• InChiKey: JTUOOBMKIGPBGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  氨氯地平杂质20 在 双氧水 、 sodium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以90%的产率得到diethyl 2,6-dimethyl-4-(2-chlorophenyl)-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  NaI易于在室温下用过氧化氢介导Hantzsch 1,4-二氢吡啶的氧化芳构化：绿色程序

  摘要：

  使用催化量的NaI和H 2 O 2（30％）作为绿色外部氧化剂，可以轻松实现1,4-二氢吡啶的氧化转化，从而以优异的收率得到相应的吡啶衍生物。该方法是高度绿色的，其中在将冰水添加到反应混合物中之后，容易将固体产物滤出。这种非过渡金属催化剂具有成本效益，提供了简单的后处理和易于分离的产物。

  DOI：

  10.1007/bf03246562

文献信息

• Aromatization of Hantzsch 1,4-Dihydropyridines with I2-MeOH
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Gowravaram Sabitha、Garudammagari S. Kiran Kumar Reddy

  DOI：10.1055/s-2000-7613

  日期：——

  4-Alkyl or aryl substituted Hantzsch 1,4-dihydropyridines are aromatized to the corresponding pyridines in high yields by iodine in refluxing methanol. The method tolerates several substituents such as alkyl, benzyl, aryl and heterocyclic groups present in the 4-position of pyridines.

  4-烷基或芳基取代的 Hantzsch 1,4-二氢吡啶通过碘在回流甲醇中以高产率芳构化为相应的吡啶。该方法容许存在于吡啶的 4 位上的几个取代基，例如烷基、苄基、芳基和杂环基团。
• Biomimetic aromatization of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a new polystyrene-bound manganese porphyrin
  作者：Majid Moghadam、Masoud Nasr-Esfahani、Shahram Tangestaninejad、Valiollah Mirkhani、Mohammad Ali Zolfigol

  DOI：10.1139/v05-255

  日期：2006.1.1

  Efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a polystyrene-bound manganese(III) porphyrin is reported. This catalyst shows high activity in the oxidation of various 1,4-dihydropyridines at room temperature. This heterogeneous catalyst can be reused five times without significant loss of its activity.Key words: biomimetic oxidation, supported metalloporphyrin, periodate, 1,4-dihydropyridine.

  报道了聚苯乙烯-锰(III)卟啉催化的过氧化钠对Hantzsch 1,4-二氢吡啶的高效氧化。该催化剂在室温下对各种1,4-二氢吡啶的氧化表现出高活性。这种非均相催化剂可重复使用五次而不显著降低其活性。关键词：仿生氧化，支持金属卟啉，过碘酸盐，1,4-二氢吡啶。
• Rapid and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by manganese (III) Schiff base complexes
  作者：Masoud Nasr-Esfahani、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Ahmad Reza Momeni

  DOI：10.1016/j.bmc.2005.11.051

  日期：2006.4

  Rapid and efficient oxidation of Hantzsch 1,4-dihydropyridine with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system converts 1,4-dihydropyridines to their corresponding pyridine derivatives at room temperature in a 1:1, CH3CN/H2O mixture. The ability of various Schiff base complexes in the oxidation of 1,4-dihydropyridine was also investigated.

  据报道，高碘酸钠可快速有效地氧化Hantzsch 1,4-二氢吡啶。Mn（III）-salophen / NaIO4催化体系在室温下以1：1的CH3CN / H2O混合物将1,4-二氢吡啶转化为其相应的吡啶衍生物。还研究了各种席夫碱配合物在1,4-二氢吡啶氧化中的能力。
• Efficient Oxidation of Hantzsch 1,4-Dihydropyridines with Tetrabutylammonium Peroxomonosulfate Catalyzed by Manganese(III) Schiff Base Complexes: The Effect of Schiff Base Complex on the Product Selectivity
  作者：Masoud Nasr-Esfahani、Majid Moghadam、Ghasem Valipour

  DOI：10.1080/00397910902838995

  日期：2009.10.12

  Abstract Efficient and rapid oxidation of Hantzsch 1,4-dihydropyridine with tetrabutylammonium peroxomonosulfate (TBAO) is reported. The Mn(salophen)/monopersulfate catalytic system efficiently converts 1,4-dihydropyridines (DHPs) to their corresponding pyridine derivatives under mechanical stirring and microwave irradiation in CH2Cl2. The ability of various Schiff base complexes to oxidize DHPs was

  摘要 报道了用四丁基过氧单硫酸铵 (TBAO) 高效快速氧化 Hantzsch 1,4-二氢吡啶。Mn(salophen)/单过硫酸盐催化体系在机械搅拌和微波照射下在 CH2Cl2 中有效地将 1,4-二氢吡啶 (DHP) 转化为其相应的吡啶衍生物。还研究了各种席夫碱复合物氧化 DHP 的能力。结果表明，在锰席夫络合物的存在下，没有得到副产物。
• Catalytic Effect of Basic Alumina in the Dehydrogenation of 1,4-Dihydropyridines with Tetrabutylammonium Peroxydisulfate
  作者：Hamid R. Memarian、Behjat Barati

  DOI：10.1515/znb-2010-0914

  日期：2010.9.1

  4-Alkyl- or 4-aryl-1,4-dihydropyridine derivatives were oxidized to the pyridine derivatives by tetrabutylammonium peroxydisulfate (n-Bu₄N)₂S₂O₈ (TBAPD) in combination with basic alumina in refluxing acetonitrile and also in the absence or presence of basic alumina under microwave irradiation. The presence of basic alumina plays an important role in the reaction mechanism. Whereas oxidation under thermal condition is assumed to occur through an ionic mechanism, ionic and also radical mechanisms are proposed for the reactions under microwave irradiation.

  4-烷基或4-芳基-1,4-二氢吡啶衍生物通过四丁基铵过二硫酸酯（n-Bu₄N)₂S₂O₈（TBAPD）与碱性氧化铝在回流的乙腈中氧化为吡啶衍生物，也可以在微波辐射下，在有无碱性氧化铝的情况下进行。碱性氧化铝的存在在反应机制中起着重要作用。在热条件下进行氧化被认为是通过离子机制发生的，而在微波辐射下进行的反应则提出了离子和自由基机制。