1,1'-(4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-diyl)diethanone | 86524-62-1

• 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: 1,1'-(4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-diyl)diethanone
• 英文别名: 3,5-diacetyl-2,6-dimethyl-4-(4-methoxyphenyl)pyridine；3,5-diacetyl-4-(4-methoxyphenyl)-2,6-dimethylpyridine；1-[5-acetyl-4-(4-methoxyphenyl)-2,6-dimethylpyridin-3-yl]ethanone
• CAS: 86524-62-1
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: XMFHQVXGRZIDQP-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165 °C(Solv: ethanol (64-17-5))
• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  3,5-diacetyl-4-(4-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine 在 双氧水 作用下， 以 乙腈 为溶剂， 反应 25.0h， 以98%的产率得到1,1'-(4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-diyl)diethanone
  参考文献：
  名称：

  硅氧钒酸[SiO 2 -VO（OH）2]作为非均相和可循环利用的催化剂，用于室温下汉茨1,4-二氢吡啶的氧化芳构化

  摘要：

  描述了一种在室温下使用过氧化氢作为绿色氧化剂，硅氧钒为催化剂在乙腈中将Hantzsch 1,4-二氢吡啶氧化芳香化为相应吡啶的简单方法。催化剂可以很容易地回收并重复使用15个反应周期，而不会损失活性。

  DOI：

  10.1007/s13738-014-0431-9

文献信息

• A simple, efficient, one-pot three-component domino synthesis of Hantzsch pyridines under solvent-free condition
  作者：Masoud Nasr-Esfahani、Bahador Karami、Masoume Behzadi

  DOI：10.1002/jhet.175

  日期：2009.9

  In this article, efficient and simple preparation of Hantzsch pyridine derivatives by reaction of various aldehydes and β-dicarbonyls in the presence of ammonium chlorate under solvent-free condition at 80°C is reported. The advantages of this system are the one-step procedure, high yields of the products, and the ability to carry out large-scale reactions. J. Heterocyclic Chem., (2009).

  在本文中，通过在乙腈存在下各种醛与β-二羰基的反应，可以有效而简单地制备Hantzsch吡啶衍生物 据报道在80°C无溶剂条件下的氯酸铵。该系统的优势在于一步法，高收率的产品以及进行大规模反应的能力。J.杂环化​​学，（2009）。
• 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。
• Application of silica vanadic acid [SiO2-VO(OH)2] as a heterogeneous and recyclable catalyst for oxidative aromatization of Hantzsch 1,4-dihydropyridines at room temperature
  作者：Maliheh Safaiee、Mohammad Ali Zolfigol、Mahsa Tavasoli、Mohammad Mokhlesi

  DOI：10.1007/s13738-014-0431-9

  日期：2014.12

  A simple method for the oxidative aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridines is described using hydrogen peroxide as green oxidant and silica vanadic acid as catalyst in acetonitrile at room temperature. The catalyst can be easily recovered and reused for 15 reaction cycles without considerable loss of activity.

  描述了一种在室温下使用过氧化氢作为绿色氧化剂，硅氧钒为催化剂在乙腈中将Hantzsch 1,4-二氢吡啶氧化芳香化为相应吡啶的简单方法。催化剂可以很容易地回收并重复使用15个反应周期，而不会损失活性。
• 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。