ethyl 4-(4-methoxyphenyl)-2-oxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 388-03-4

• 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: ethyl 4-(4-methoxyphenyl)-2-oxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester；4-(4-Methoxy-phenyl)-2-oxo-6-trifluormethyl-1,2,3,4-tetrahydro-pyrimidin-5-carbonsaeure-aethylester
• CAS: 388-03-4
• 化学式: C₁₅H₁₅F₃N₂O₄
• 分子量: 344.29
• InChiKey: XMMLKPIADPOSHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  384.6±42.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-methoxyphenyl)-2-oxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以76%的产率得到ethyl 4-(4-methoxyphenyl)-6-trifluoromethyl-pyrimidin-2(1H)-one-5-carboxylate
  参考文献：
  名称：

  Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.07.063
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 三氟乙酰乙酸乙酯 、 尿素 在 氢氟酸 作用下， 以 水 为溶剂， 反应 0.33h， 以86%的产率得到ethyl 4-(4-methoxyphenyl)-2-oxo-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  新型 6-(三氟甲基)-1, 2, 3, 4-四氢嘧啶-5-羧酸衍生物的多组分合成和抗癌活性研究

  摘要：

  摘要 以 4,4,4-三氟-3-氧代丁酸乙酯、脲和芳基醛为原料，以良好的收率获得了一系列新型 6-(三氟甲基)-1,2,3,4-四氢嘧啶-5-羧酸酯衍生物。 Biginelli 多组分反应。针对四种人类癌细胞系（A549、HepG2、COLO205 和 DU145）对所有相应的产物 4a-4p 进行了检查，并已鉴定出具有良好抗癌活性的化合物 4e、4i 和 4m。图形概要

  DOI：

  10.1080/00397911.2018.1490769

文献信息

• Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate†
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Kasireddy Bhaskar Reddy、Kavuda Sarita Raj、Attaluri R. Prasad

  DOI：10.1039/b102565c

  日期：——

  Ceric ammonium nitrate efficiently catalyzes the three component condensation of an aldehyde, β-ketoester and urea in methanol to afford the corresponding dihydropyrimidinones in excellent yields under sonication. Other oxidants such as manganese triacetate and Oxone were also found to catalyze this transformation under similar conditions.

  铈铵硝酸盐有效催化醛、β-酮酯和尿素在甲醇中的三组分缩合反应，生成相应的二氢嘧啶酮，产率优秀，并在超声条件下进行。其他氧化剂，如醋酸锰三乙酯和Oxone，也在类似条件下催化了这一转化反应。
• An unusual oxidation–dealkylation of 3,4-dihydropyrimidin-2(1H)-ones mediated by Co(NO3)2·6H2O/K2S2O8 in aqueous acetonitrile
  作者：Pachaiyappan Shanmugam、Paramasivan T. Perumal

  DOI：10.1016/j.tet.2006.11.010

  日期：2007.1

  4-Aryl-6-methyl-3,4-dihydropyrimidin-2(1H)-one (DHPM) scaffolds of Biginelli type were oxidized using Co(II)/S2O82- and the reaction afforded 6-unsubstituted pyrimidin-2(1H)-ones through an unprecedented dealkylation process. 4-Alkyl DHPMs under similar conditions afforded yet another unusual product, ethyl tetrahydropyrimidin-2,4(1H,3H)-dione-5-carboxylate. (c) 2006 Elsevier Ltd. All rights reserved.