diethyl 2,6-dimethyl-4-(m-methoxyphenyl)pyridine-3,5-dicarboxylate | 128042-04-6

• 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-(m-methoxyphenyl)pyridine-3,5-dicarboxylate
• 英文别名: 4-(3-methoxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester；4-(3-Methoxy-phenyl)-2,6-dimethyl-pyridin-3,5-dicarbonsaeure-diaethylester；Diethyl 4-(3-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 128042-04-6
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: SUOUTWRQFDHFAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2,6-dimethyl-4-(m-methoxyphenyl)pyridine-3,5-dicarboxylate 在 氢氧化钾 作用下， 生成 4-(3-methoxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid monoethyl ester
  参考文献：
  名称：

  Kahn et al., Journal of the Chemical Society, 1949, p. 2128,2133

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 在 四氯化锡 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 diethyl 2,6-dimethyl-4-(m-methoxyphenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Jain; Kant; Dhar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 3, p. 277 - 279

  摘要：

  DOI：

文献信息

• Electron Transfer-induced Aromatization of 1,4-Dihydropyridines
  作者：Hamid R. Memarian、Marieh Ghazaie、Somayeh Kakhki Mehneh

  DOI：10.1515/znb-2009-1012

  日期：2009.10.1

  A wide variety of 3,5-dicarboethoxy-1,4-dihydropyridines and 3,5-diacetyl-1,4-dihydropyridines are aromatized to the pyridine derivatives by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at room temperature and under microwave irradiation. An electron transfer-induced mechanism is proposed for this reaction which is influenced by the nature of the solvent, the nature of the substituents located on 3-, 4- and 5-positions of the 1,4-dihydropyridine ring, and the presence of oxygen or argon atmosphere.

  一种广泛的3,5-二乙酰基-1,4-二氢吡啶和3,5-二酯基-1,4-二氢吡啶在室温和微波辐射下，通过2,3-二氯-5,6-二氰-p-苯醌（DDQ）被芳构化为吡啶衍生物。本反应提出了一种受电子转移诱导的机制，该机制受溶剂性质、位于1,4-二氢吡啶环的3、4和5位取代基的性质以及氧气或氩气氛围的影响。
• Oxidation of 1,4-Dihydropyridines and 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones to Substituted Pyridines and Pyrimidinones Using Ca(OCl)₂in Aqueous Media
  作者：Fatemeh Tamaddon、Zahra Razmi

  DOI：10.1080/00397911003587523

  日期：2011.1.31

  [image omitted] 1,4-Dihydropyridines and 3,4-dihydropyrimidin-2(1H)-ones obtained from the Hantzsch and Biginelli reactions undergo readily oxidative dehydrogenation by using calcium hypochlorite in very short times. These calcium stimulator drugs were oxidized under reaction conditions next to the in vivo transformations at room temperature.
• Biomimetic Aromatization of Hantzsch 1,4-Dihydropyridines by S-S Bonds under Mild Conditions
  作者：Hamid Aliyan、Razieh Fazaeli、Ahmad Reza Moemeni、Ahmad Reza Massah、Hamid Javaherian Naghash、Fattaneh Khosravi

  DOI：10.3987/com-07-11030

  日期：——

  For the first time Hantzsch 1,4-dihydropyridines were oxidized to the corresponding pyridines by diphenyl disulfide in ionic liquid.
• Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines Catalyzed by Ferric Perchlorate in Ionic Liquids with Air
  作者：Dan Liu、Jianzhou Gui、Chan Wang、Feng Lu、Yulian Yang、Zhaolin Sun

  DOI：10.1080/00397910903029925

  日期：2010.3.12

  A variety of Hantzsch 1,4-dihydropyridines were oxidized to the corresponding pyridines catalyzed by a catalytic amount of ferric perchlorate. The reaction was carried out in ionic liquid at room temperature, and the products were isolated in good to excellent yields. At the same time, the catalytic system was found to be reusable.
• Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid
  作者：Majid M. Heravi、Farahnaz K. Behbahani、Hossien A. Oskooie、Rahim Hekmat Shoar

  DOI：10.1016/j.tetlet.2005.02.147

  日期：2005.4

  Catalytic oxidation of Hantzsch 1,4-dihydropyridines is described using a catalytic amount of ferric perchlorate in acetic acid at room temperature. (c) 2005 Published by Elsevier Ltd.