3,5-diacetyl-4-(o-methoxyphenyl)-2,6-dimethylpyridine | 546123-78-8

• 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: 3,5-diacetyl-4-(o-methoxyphenyl)-2,6-dimethylpyridine
• 英文别名: 3,5-diacetyl-4-(2-methoxyphenyl)-2,6-dimethylpyridine；1-[5-acetyl-4-(2-methoxyphenyl)-2,6-dimethylpyridin-3-yl]ethanone
• CAS: 546123-78-8
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: IHBZEXBTSMWAJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 3,5-diacetyl-4-(o-methoxyphenyl)-2,6-dimethylpyridine 在 sodium perchlorate 作用下， 生成 3,5-diacetyl-4-(o-methoxyphenyl)-1,2,6-trimethylpyridinium perchlorate
  参考文献：
  名称：

  Recyclization of polysubstituted pyridinium salts

  摘要：

  3,5-Diacetyl- and 3,5-dicyano-1,2,6-trimethylpyridinium perchlorates are converted by recyclization into N,5-dimethylanilines and 2-methylaminopyridines, respectively.

  DOI：

  10.1016/0040-4020(95)00474-m
• 作为产物：
  描述：

  3,5-diacetyl-4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine 在 (Bu₄N)₂S₂O₈ 作用下， 以 乙腈 为溶剂， 反应 0.02h， 生成 3,5-diacetyl-4-(o-methoxyphenyl)-2,6-dimethylpyridine
  参考文献：
  名称：

  Catalytic Effect of Basic Alumina in the Dehydrogenation of 1,4-Dihydropyridines with Tetrabutylammonium Peroxydisulfate

  摘要：

  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。

  DOI：

  10.1515/znb-2010-0914

文献信息

• Synthesis and Photochemistry of Novel 3,5-Diacetyl-1,4-dihydropyridines. II [1]
  作者：Hamid R. Memarian、Mohammad Bagheri、Dietrich D�pp

  DOI：10.1007/s00706-003-0139-5

  日期：2004.6

  In continuation of previous work some novel 3,5-diacetyl-1,4-dihydropyridine derivatives were synthesized and their photochemical behavior was studied under oxygen and argon atmosphere. Oxidation of the dihydropyridine ring and formation of pyridine derivatives was the result of the reaction. The presence of oxygen affects not only on the rate of oxidation, but also the formation of some unidentified

  在先前工作的基础上，合成了一些新颖的3,5-二乙酰基-1,4-二氢吡啶衍生物，并在氧气和氩气气氛下研究了它们的光化学行为。该反应的结果是二氢吡啶环的氧化和吡啶衍生物的形成。氧的存在不仅影响氧化速率，而且在这种气氛下照射时观察到一些未鉴定的副产物的形成。
• 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。
• 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。
• Aromatization of 1,4-dihydropyridines in the presence of methanesulfonic acid/NaNO₂/wet SiO₂under both heterogeneous and solvent free conditions
  作者：Khodabakhsh Niknam、Seyed Mehdi Razavian、Mohammah Ali Zolfigol、Iraj Mohammahpoor-Baltork

  DOI：10.1002/jhet.5570430131

  日期：2006.1

  A combination of methanesulfonic acid and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of 1,4-dihydropyridines to the corresponding pyridine derivatives under mild and heterogeneous conditions in excellent yields.

  在湿的SiO 2存在下，将甲磺酸和亚硝酸钠的混合物用作有效的氧化剂，用于在温和和非均相条件下以极好的收率将1,4-二氢吡啶氧化为相应的吡啶衍生物。
• Solid state photochemistry of 1,4-dihydropyridines
  作者：Hamid R. Memarian、Arsalan Mirjafari

  DOI：10.1016/j.bmcl.2005.05.026

  日期：2005.7

  Photochemical behavior of some 1,4-dihydropyridines has been investigated in the solid state. Whereas upon irradiation of 1,4-dihydropyridines in solution phase, their photo-oxidation and formation of pyridine derivatives have been observed, irradiation of these compounds in the solid state decreases their light sensitivity. In many cases photo-oxidation has been observed only in very low yields.

  已经研究了固态的一些1,4-二氢吡啶的光化学行为。尽管在溶液相中辐射1，4-二氢吡啶时，已经观察到它们的光氧化和吡啶衍生物的形成，但是以固态辐射这些化合物降低了它们的光敏性。在许多情况下，仅以非常低的产率观察到光氧化。