ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate | 95928-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate
• 英文别名: ethyl 1,6-dimethyl-4-phenyl-pyrimidin-2(1H)-one-5-carboxylate；5-ethoxycarbonyl-1,6-dimethyl-4-phenylpyrimidin-2-one；1,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester；Ethyl 1,2-dihydro-1,6-dimethyl-2-oxo-4-phenyl-5-pyrimidinecarboxylate；ethyl 1,6-dimethyl-2-oxo-4-phenylpyrimidine-5-carboxylate
• CAS: 95928-50-0
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: ODZSSTNNELAFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate 在 碘 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 27.0h， 以62%的产率得到ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  镁/甲醇：一种化学选择性还原嘧啶-2（1 H）-ones的有效还原剂

  摘要：

  甲醇中的镁是化学选择性还原嘧啶2（1 H）-ones的有效试剂。其他可还原的官能团，例如烯胺酯和乌里多羰基的酯和烯烃，不受影响。这构成了通过嘧啶-2（1 H）-one的还原形成Biginelli 3,4-dihydropyrimidin-2（1 H）one的第一个例子。

  DOI：

  10.1016/j.tetlet.2009.02.165
• 作为产物：
  描述：

  ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以60%的产率得到ethyl 1,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  An Efficacious Protocol for the Oxidation of 3,4-Dihydropyrimidin-2(1H)-ones using Pyridinium Chlorochromate as Catalyst

  摘要：

  在中性条件下，使用氯铬酸吡啶鎓对 4-未取代的以及 4,6- 芳基/烷基-3,4-二氢嘧啶-2(1H)-酮进行氧化，以合成有用的方式获得相应的嘧啶-2(1H)-酮。

  DOI：

  10.1071/ch07432

文献信息

• An Efficacious Protocol for the Oxidation of 3,4-Dihydropyrimidin-2(1H)-ones using Pyridinium Chlorochromate as Catalyst
  作者：Kamaljit Singh、Kawaljit Singh

  DOI：10.1071/ch07432

  日期：——

  4-Unsubstituted as well as 4,6-aryl/alkyl-3,4-dihydropyrimidin-2(1H)-ones were oxidized under neutral conditions using pyridinium chlorochromate to obtain the corresponding pyrimidin-2(1H)-ones in a synthetically useful manner.

  在中性条件下，使用氯铬酸吡啶鎓对 4-未取代的以及 4,6- 芳基/烷基-3,4-二氢嘧啶-2(1H)-酮进行氧化，以合成有用的方式获得相应的嘧啶-2(1H)-酮。
• Substituent effects on the voltammetric studies of 2-oxo-1,2,3,4-tetrahydropyrimidines
  作者：Hamid R. Memarian、Mahnaz Ranjbar、Hassan Sabzyan、Abolfazl Kiani

  DOI：10.1016/j.crci.2012.09.009

  日期：2012.11

  nature and steric hindrance of the substituents, their positions and their orientations towards the heterocyclic ring, determine their effects on the oxidation peak potential. The electron detachment process in this study is also affected by the nature of solvent, which explains the extent of solvation of both neutral THPM and THPṀ + . Analysis of the computational results obtained at the DFT-B3LYP/6-31++G**

  摘要 使用伏安法在玻碳电极上研究了各种取代的 2-oxo-1,2,3,4-四氢嘧啶 (THPM) 在乙腈中的电化学氧化，以研究取代基对 1- 、 4- 和 5- 位的杂环。对本研究中提出的结果的分析表明，取代基的电子性质和位阻、它们的位置和它们对杂环的取向，决定了它们对氧化峰电位的影响。本研究中的电子脱离过程也受溶剂性质的影响，这解释了中性 THPM 和 THPṀ + 的溶剂化程度。对在 DFT-B3LYP/6-31++G** 理论水平上获得的计算结果的分析表明了一种机制，其中第一次电子去除发生在 N1 原子上。此过程之后是快速去除质子，导致形成稳定的烯丙基和/或苄基自由基，然后进一步氧化成 2-氧代-1,2-二氢嘧啶 (DHPM)。
• On the reaction of 3,4-dihydropyrimidones with nitric acid. Preparation and x-ray structure analysis of a stable nitrolic acid
  作者：Agnieszka Puchala、Ferdinand Belaj、C. Oliver Kappe、Jan Bergman

  DOI：10.1002/jhet.5570380616

  日期：2001.11

  4-dihydro-2-pyrimidones (DHPMs) was reacted with nitric acid under different reaction conditions. Treatment of DHPMs with 50-65% nitric acid at 0 °C led to the formation of the corresponding dehydrogenated 2-pyrimidones in moderate to good yields. In contrast, reaction of one representative DHPM with 60% nitric acid at 50 °C led to an unusually stable nitrolic acid, involving a formal nitration, nitrosation, and

  在不同的反应条件下，一系列取代的3,4-二氢-2-嘧啶酮（DHPM）与硝酸反应。在0°C下用50-65％的硝酸处理DHPM导致以中等至良好的产率形成相应的脱氢2-嘧啶酮。相反，一种代表性的DHPM与60％的硝酸在50°C的反应导致异常稳定的硝酸，涉及正式的硝化，亚硝化和脱氢步骤。该产物的分子结构通过X射线晶体学分析确定
• Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate
  作者：P. Shanmugam、P.T. Perumal

  DOI：10.1016/j.tet.2006.07.063

  日期：2006.10

  Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• Substituent effect in photocatalytic oxidation of 2-oxo-1,2,3,4-tetrahydropyrimidines using TiO2 nanoparticles
  作者：Hamid R. Memarain、Mahnaz Ranjbar

  DOI：10.1016/j.molcata.2011.12.026

  日期：2012.4

  The semiconductor-sensitized oxidation of various 1-, 4- and 5-substituted 2-oxo-1,2,3,4-tetrahydropyrimidines was carried out in acetonitrile using TiO2 anatase nanoparticles. The aims of this study were to elucidate the effects of the nature of the substituents on the 1-, 4- and 5-positions of the heterocyclic ring, the type of the photocatalyst and the nature of solvent on the rate of reaction. The proposed electron-transfer mechanism is supported by the experimental results and also by the computational studies. (C) 2012 Elsevier B.V. All rights reserved.