diethyl 4-phenylpyridine-3,5-dicarboxylate

• 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 4-phenylpyridine-3,5-dicarboxylate
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: RYWQLXAWRCFWRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2,6-二甲基-4-苯基-1,4-二氢吡啶-3,5-二羧酸二乙酯 在 硝基脲 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以99%的产率得到diethyl 4-phenylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Metal-Free Oxidation of Urazole and 1,4-Dihydropyridine Derivatives Under Mild and Heterogeneous Conditions by Nitro Urea, Derived from Urea Nitrate, and Silica Sulfuric Acid

  摘要：

  温和组合的硝基脲（源自尿 nitrate）和硅酸硫（SiO2OSO3H）可能作为一种有效的氧化介质，能够氧化多种类型的杂环化合物，包括脲唑和1,4-二氢吡啶。这里提出的过程操作简单、环境友好，反应在室温下于二氯甲烷中温和进行。

  DOI：

  10.2174/157017810791112450

文献信息

• Thioacetamide as an Ammonium Source for Multicomponent Synthesis of Pyridines from Aldehydes and Electron-Deficient Enamines or Alkynes
  作者：Jie-Ping Wan、Youyi Zhou、Kezhi Jiang、Hongyan Ye

  DOI：10.1055/s-0034-1378635

  日期：——

  for the synthesis of pyridines. In the reactions, thioacetamide is used as a cheap and efficient ammonium source in a multicomponent reaction with aldehydes and electron-deficient enamines or alkynes to give 3,4,5-trisubstituted pyridines in moderate to good yields and with a high product diversity. A generally applicable multicomponent method has been established for the synthesis of pyridines. In the

  摘要 已经建立了用于吡啶合成的普遍适用的多组分方法。在反应中，硫代乙酰胺在与醛和缺电子的烯胺或炔烃的多组分反应中用作廉价高效的铵源，以中等至良好的收率和较高的产物多样性得到3,4,5-三取代的吡啶。 已经建立了用于吡啶合成的普遍适用的多组分方法。在反应中，硫代乙酰胺在与醛和缺电子的烯胺或炔烃的多组分反应中用作廉价高效的铵源，以中等至良好的收率和较高的产物多样性得到3,4,5-三取代的吡啶。
• Synthesis of 1,4-Dihydropyridines and Their Fluorescence Properties
  作者：Shunsuke Sueki、Ryo Takei、Yuto Zaitsu、Junya Abe、Akane Fukuda、Keisuke Seto、Yukio Furukawa、Isao Shimizu

  DOI：10.1002/ejoc.201402426

  日期：2014.8

  We have successfully synthesized 3,4,5-substituted 1,4-dihydropyridines (1,4-DHPs) from amine hydrochloride salts, aldehydes, and acetals in good yields without the addition of a catalyst. The synthesized 1,4-DHPs exhibit various wavelengths of fluorescence, which could be tuned by changing the substituents at the 3- and 5-positions of the 1,4-DHPs.

  我们已经成功地从胺盐酸盐、醛和缩醛中合成了 3,4,5-取代的 1,4-二氢吡啶 (1,4-DHPs)，且收率良好，无需添加催化剂。合成的 1,4-DHPs 显示出不同波长的荧光，可以通过改变 1,4-DHPs 3-和 5-位的取代基来调节。
• Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study
  作者：Qiangwen Fan、Hongbo Tan、Peng Li、Hong Yan

  DOI：10.1039/c8nj02192a

  日期：——

  In this article, the hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) in solution was reported, wherein head-to-tail (HT) dimeric products (syn-dimers and cage dimers) were formed exclusively through successive inter- and intra-molecular [2+2] cycloaddition. The effects of irradiation wavelength, solvents and substituents on the efficiency of these transformations were

  在本文中，在异质的分子间[2 + 2]的溶液中1,4-二氢吡啶（1,4-DHP类）光环被报道，其特征在于，头-尾（HT）的二聚产物（顺式-dimers和笼二聚体）仅通过连续的分子间和分子内[2 + 2]环加成反应形成。研究了辐照波长，溶剂和取代基对这些转化效率的影响。为了阐明光环加成反应的内在特征和立体选择性，进行了DFT和TDDFT理论计算，以揭示详细的反应过程。
• Novel solid-state synthesis of dimeric 4-aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Frank W. Heinemann

  DOI：10.1002/jhet.5570350217

  日期：1998.3

  On irradiation in the solid state the 4-aryl-1,4-dihydroypridines 1 undergo [2+2] cycloadditon to centrosymmetric head-to-tail dimers 3 and 4a. The almost exclusive formation of the cage dimers 3 via the C2-symmetric syn-dimers 2 takes place in nearly quantitative yields, in contrast with the cycloaddition reaction of the anti-dimer 4a, which is accompanied by photooxidation to pyridine 5a.

  在固态辐射下，4-芳基-1,4-二氢吡啶1经历[2 + 2]环二酮至中心对称的头对尾二聚体3和4a。该笼二聚体几乎只形成3 经由与c 2 -对称顺-dimers 2发生在几乎定量的产率，在与所述的环加成反应对比度抗-dimer 4a中，这是伴随着光氧化，以吡啶5a中。
• Investigating the Existence of Nonthermal/Specific Microwave Effects Using Silicon Carbide Heating Elements as Power Modulators
  作者：Tahseen Razzaq、Jennifer M. Kremsner、C. Oliver Kappe

  DOI：10.1021/jo8009402

  日期：2008.8.1

  [GRAPHICS]The use of passive heating elements made out of chemically inert sintered silicon carbide (SiC) allows microwave transparent or poorly absorbing reaction mixtures to be heated under microwave conditions. The cylindrical heating inserts efficiently absorb microwave energy and subsequently transfer the generated thermal energy via conduction phenomena to the reaction mixture. In the case of low to medium microwave absorbing reaction mixtures, the addition of SiC heating elements results in significant reductions (30-70%) in the required microwave power as compared to experiments performed without heating element at the same temperature. The method has been used to probe the influence of microwave power (electromagnetic field strength) on chemical reactions. Six diverse types of chemical transformations were performed in the presence or absence of a SiC heating element at the same reaction temperature but at different microwave power levels. In all six cases, the measured conversions/yields were similar regardless of whether a heating element was used or not. The applied microwave power had no influence on the reaction rate, and only the attained temperature governed the outcome of a specific chemical process under microwave conditions.