3,5-diacetyl-2,4,6-trimethylpyridine | 145221-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-diacetyl-2,4,6-trimethylpyridine
• 英文别名: 1-(5-acetyl-2,4,6-trimethylpyridin-3-yl)ethanone
• CAS: 145221-59-6
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: UHOZWAIMMCYWGG-UHFFFAOYSA-N

物化性质

• 沸点：
  365.2±42.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-diacetyl-2,4,6-trimethylpyridine 、 硫酸二甲酯 生成 3,5-diacetyl-1,2,4,6-tetramethyl-pyridinium; perchlorate
  参考文献：
  名称：

  Mumm; Petzold, Justus Liebigs Annalen der Chemie, 1938, vol. 536, p. 1,22

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-丁二酮-2,4,6-三甲基-1,4-羟基吡啶 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 0.03h， 以95%的产率得到3,5-diacetyl-2,4,6-trimethylpyridine
  参考文献：
  名称：

  Electron Transfer-induced Aromatization of 1,4-Dihydropyridines

  摘要：

  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。

  DOI：

  10.1515/znb-2009-1012

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。
• Microwave Heating in Conjunction with UV Irradiation: a Tool for the Oxidation of 1,4-Dihydropyridines to Pyridines
  作者：Chad M. Kormos、Rachel M. Hull、Nicholas E. Leadbeater

  DOI：10.1071/ch08414

  日期：——

  Microwave heating is used for the preparation of 1,4-dihydropyridines and then, in conjunction with UV irradiation, is used for the efficient oxidation of the 1,4-dihydropyridines to pyridines. The oxidation reactions are performed in a sealed vessel using oxygen as the oxidant and an electrodeless discharge lamp as the irradiation source.

  微波加热用于制备 1,4-二氢吡啶，然后结合紫外线照射，将 1,4-二氢吡啶高效氧化为吡啶。氧化反应在密封容器中进行，使用氧气作为氧化剂，无极放电灯作为辐照源。
• 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。
• Preparation of New Organic Luminophores Based on 3,5-Diacetylpyridines
  作者：Pavel Lhoták、Antonín Kurfürst

  DOI：10.1135/cccc19921937

  日期：——

  The reaction of acetylacetone or sodium salt of oxymethyleneacetone with corresponding aldehydes has been used to prepare 3,5-diacetyl-1,4-dihydropyridines III which have been oxidized to diacetylpyridines VII. These compounds have been transformed by an acid-catalyzed reaction with benzaldehyde into the chalcones VIII which have been utilized for the Kröhnke synthesis of luminophoric terpyridines I and II.

  已经使用乙酰丙酮或氧亚甲基丙酮钠盐与相应的醛反应来制备3,5-二乙酰-1,4-二氢吡啶III，这些化合物已经被氧化成二乙酰吡啶VII。这些化合物经过酸催化与苯甲醛反应转化为香豆素VIII，用于合成发光吡啶I和II的Kröhnke合成。