ethyl 6-methyl-4-(2-furyl)pyrimidin-2(1H)-one-5-carboxylate | 1451203-39-6

• 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 6-methyl-4-(2-furyl)pyrimidin-2(1H)-one-5-carboxylate
• 英文别名: ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate；Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate；ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1H-pyrimidine-5-carboxylate
• CAS: 1451203-39-6
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: ZQKLNEFLIOTAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 6-methyl-4(fur-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.42h， 以90%的产率得到ethyl 6-methyl-4-(2-furyl)pyrimidin-2(1H)-one-5-carboxylate
  参考文献：
  名称：

  Novel and Chemoselective Dehydrogenation of 3,4-Dihydropyrimidin-2(1H)-ones with 1,4-Bis(triphenylphosphonium)-2-butene Peroxodisulfate

  摘要：

  3,4-二氢嘧啶-2(1H)-酮在1,4-双(三苯基膦)-2-丁烯过硫酸盐水溶液乙腈中处理下，短时间内高效转化为相应的嘧啶-2(1H)-酮，产率很高。该试剂还能在其他可氧化官能团的存在下实现3,4-二氢嘧啶的选择性氧化。

  DOI：

  10.5012/bkcs.2013.34.6.1751

文献信息

• Discovery of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones As a Novel Class of Potent and Selective A_2B Adenosine Receptor Antagonists
  作者：Abel Crespo、Abdelaziz El Maatougui、Pierfrancesco Biagini、Jhonny Azuaje、Alberto Coelho、José Brea、María Isabel Loza、María Isabel Cadavid、Xerardo García-Mera、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/ml400185v

  日期：2013.11.14

  We describe the discovery and optimization of 3,4-dihydropyrimidin-2(1H)-ones as a novel family of (nonzanthine) A(2B) receptor antagonists that exhibit an unusually high selectivity profile. The Biginelli-based hit optimization process enabled a thoughtful exploration of the structure-activity and structure-selectivity relationships for this chemotype, enabling the identification of ligands that combine structural simplicity with excellent hA(2B) AdoR affinity and remarkable selectivity profiles.
• 4-Bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient oxidizing agent for one-pot synthesis of ethyl pyrimidin-2(1H)-one-5-carboxylates
  作者：M. Gorjizadeh、M. Afshari

  DOI：10.1134/s1070363217040284

  日期：2017.4

  An efficient one-pot synthesis of pyrimidin-2(1H)-ones via three-component condensation of aldehyde, ethyl acetoacetate and urea using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate [BTPBPDS] as an oxidant is described.