5-acetyl-4-(4'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one | 1091909-54-4

• 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-(4'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one
• 英文别名: 5-acetyl-4-(4-methoxyphenyl)-6-methyl-1H-pyrimidin-2-one
• CAS: 1091909-54-4
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: CAWZGMBDHSYJKJ-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

• 作为反应物：
  描述：

  5-acetyl-4-(4'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.58h， 生成 1-(4-(4-methoxyphenyl)-6-methyl-2-(thiophen-2-yl)pyrimidin-5-yl)ethanone
  参考文献：
  名称：

  Efficient synthesis of diversely substituted pyrimidines by palladium catalyzed Suzuki–Miyaura coupling

  摘要：

  An efficient synthesis of 2-aryl/heteroaryl substituted pyrimidinyl ethanones 4(a-t) was developed using a palladium-catalyzed Suzuki-Miyaura coupling reaction strategy. Use of Pd(OAc)(2) in the presence of PPh3 and Na2CO3 in 1,4-dioxane solvent was found to be the most effective reaction condition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.042
• 作为产物：
  描述：

  乙酰丙酮 在 盐酸 、 硝酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 5-acetyl-4-(4'-methoxyphenyl)-6-methylpyrimidin-2(1H)-one
  参考文献：
  名称：

  Efficient synthesis of diversely substituted pyrimidines by palladium catalyzed Suzuki–Miyaura coupling

  摘要：

  An efficient synthesis of 2-aryl/heteroaryl substituted pyrimidinyl ethanones 4(a-t) was developed using a palladium-catalyzed Suzuki-Miyaura coupling reaction strategy. Use of Pd(OAc)(2) in the presence of PPh3 and Na2CO3 in 1,4-dioxane solvent was found to be the most effective reaction condition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.042

文献信息

• Light-induced dehydrogenation of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
  作者：H. R. Memarian、M. Soleymani、H. Sabzyan

  DOI：10.1007/s13738-012-0097-0

  日期：2012.10

  an oxygen or argon atmosphere on the rate of reaction. The rate of reaction is faster under argon than under oxygen and is influenced by the nature of the substituent on the 4- and 5-positions of the THPM ring. Furthermore, it is found that the dehydrogenation of THPM-amides is faster than that of the corresponding 5-ethoxycarbonyl- and 5-acetyl-THPMs. In contrast to the solution photochemistry, no

  通过将各种2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides（THPMs）暴露于紫外光下，研究其光敏性，以阐明位于4-上的取代基的性质的影响。杂环的5-位和氧气或氩气气氛对反应速率的影响。在氩气下的反应速率比在氧气下的反应速率更快，并且受THPM环4和5位上取代基的性质影响。此外，发现THPM-酰胺的脱氢比相应的5-乙氧基羰基-和5-乙酰基-THPM的脱氢更快。与溶液光化学相反，通过固态照射没有观察到变化。
• 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。
• Photo-oxidation of 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Hamid Reza Memarian、Asadollah Farhadi、Hassan Sabzyan、Mousa Soleymani

  DOI：10.1016/j.jphotochem.2009.10.012

  日期：2010.1

  A variety of Biginelli 5-acetyl-3,4-dihydropyrimidin-2(1H)-ones are efficiently oxidized to their corresponding pyrimidin-2(1H)-one derivatives upon UV irradiation under argon atmosphere in chloroform solution. The nature of the additional substituent on the phenyl ring located on C-4 of the heterocyclic ring influences the rate of reaction. An electron-transfer induced photoreaction is proposed based

  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。
• Convergent assembly of structurally diverse quinazolines
  作者：Abel Crespo、Alberto Coelho、Paula M. Diz、Franco Fernández、Hector Novoa de Armas、Eddy Sotelo

  DOI：10.1039/c0ob00608d

  日期：——

  A convergent and versatile Vilsmeier–Haack-based carbo-annulation strategy that exhibits an unusually elevated bond-forming efficiency has been developed. By virtue of its innovative approach, structure economy and simple execution conditions the methodology reported here constitutes a very attractive protocol that enables the rapid assembly of structurally diverse quinazoline chemotypes.

  我们开发出了一种基于 Vilsmeier-Haack 的聚合且多功能的碳水化合物annulation 策略，该策略具有异常高的成键效率。凭借其创新的方法、结构经济性和简单的执行条件，本文所报道的方法构成了一种极具吸引力的方案，可快速组装出结构多样的喹唑啉化学型。
• 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：——