5-acetyl-4-(2'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one | 1194097-17-0

• 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: 5-acetyl-4-(2'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one
• 英文别名: 5-acetyl-4-(2-methoxyphenyl)-6-methyl-1H-pyrimidin-2-one
• CAS: 1194097-17-0
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: FAVCWESTJCPBGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-乙酰基-4-(2-甲氧基苯基)-6-甲基-1,2,3,4-四氢嘧啶-2-酮 以 氯仿 为溶剂， 反应 7.15h， 以92%的产率得到5-acetyl-4-(2'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one
  参考文献：
  名称：

  5-乙酰基3,4-二氢嘧啶-2（1H）-ones的光氧化

  摘要：

  在氩气中于氯仿溶液中紫外线照射后，各种Biginelli 5-乙酰基-3,4-二氢嘧啶-2（1H）-酮被有效氧化为相应的嘧啶-2（1H）-一衍生物。位于杂环的C-4上的苯环上的其他取代基的性质会影响反应速率。基于HCl和CH 2 Cl 2的形成，提出了电子转移诱导的光反应。

  DOI：

  10.1016/j.jphotochem.2009.10.012

文献信息

• Light-induced Free Radical Oxidation of 2-Oxo-1,2,3,4-tetrahydropyrimidines
  作者：Hamid Reza Memarian、Leila Hejazi、Asadallah Farhadi

  DOI：10.1515/znb-2012-0313

  日期：2012.3.1

  A variety of 4-substituted 5-acetyl- and 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyrimidines were oxidized under UV irradiation in the presence or absence of benzoyl peroxide. The nature of the substituents on the 4- and 5-positions of the heterocyclic ring affects the rate of photo-oxidation, and irradiation of these compounds in the presence of benzoyl peroxide decreases the time of reaction drastically. Removal of 4-H by a benzoyloxy radical under formation of a trihydropyrimidinoyl radical intermediate occurs in the rate-determining step. The stability of this benzylic and allylic radical intermediate is affected by the nature and the position of the additional substituent on the phenyl group located at C-4.

  一系列4-取代的5-乙酰基和5-羧乙酯基-2-氧代-1,2,3,4-四氢嘧啶在紫外辐射下在有或无苯甲酰过氧化物存在下被氧化。杂环环上4-和5-位置的取代基的性质影响光氧化的速率，这些化合物在有苯甲酰过氧化物存在下的照射显著减少了反应时间。在速率决定步骤中，苯甲酰氧自由基去除4-H形成三氢嘧啶基自由基中间体。这种苄基和烯丙基自由基中间体的稳定性受到苯基团上附加取代基的性质和位置的影响，该苯基团位于C-4。
• 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)。
• Klingebiel, Uwe; Matthes, Christoph; Ringe, Arne, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 5, p. 532 - 540
  作者：Klingebiel, Uwe、Matthes, Christoph、Ringe, Arne、Magull, Joerg

  DOI：——

  日期：——
• Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines
  作者：Hamid Reza Memarian、Nazanin Jafarpour、Asadallah Farhadi

  DOI：10.1007/s00706-011-0573-8

  日期：2012.2

  Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.
• 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.