ethyl 4-(1-methylethyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate | 198827-05-3

• 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-(1-methylethyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-4-(2-propyl)-pyrimidin-2(1H)-one-5-carboxylate；ethyl 1,2-dihydro-4-isopropyl-6-methyl-2-oxopyrimidine-5-carboxylate；Ethyl 1,2-dihydro-4-methyl-6-(1-methylethyl)-2-oxo-5-pyrimidinecarboxylate；ethyl 6-methyl-2-oxo-4-propan-2-yl-1H-pyrimidine-5-carboxylate
• CAS: 198827-05-3
• 化学式: C₁₁H₁₆N₂O₃
• 分子量: 224.26
• InChiKey: VTJGADSTGGVZHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-异丙基-6-甲基-2-氧代-1,2,3,4-四氢-5-嘧啶羧酸乙酯 在 N-羟基邻苯二甲酰亚胺 、 氧气 、 cobalt(II) diacetate tetrahydrate 作用下， 以 二氯甲烷 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 以75%的产率得到ethyl 4-(1-methylethyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Efficient aerobic oxidative dehydrogenation of dihydropyrimidinones and dihydropyrimidines

  摘要：

  4-Substituted dihydropyrimidinones and dihydropyrimidines were first efficient aerobic oxidized to the corresponding pyrimidinones and pyrimidines, respectively, in high yields by molecular oxygen in the presence of catalytic amount of N-hydroxyphthalimide (NHPI) and Co(OAc)(2) in a mild and environmental benign condition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.105

文献信息

• 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.
• Synthesis and Aromatization of Dihydropyrimidines Structurally Related to Calcium Channel Modulators of the Nifedipine-Type
  作者：C. Oliver Kappe、Jean Jacques Vanden Eynde、Nancy Audiart、Valérie Canonne、Sophie Michel、Yves Van Haverbeke

  DOI：10.3987/com-97-7931

  日期：——
• Efficient aerobic oxidative dehydrogenation of dihydropyrimidinones and dihydropyrimidines
  作者：Bing Han、Run-Feng Han、Yu-Wei Ren、Xiao-Yong Duan、Yi-Chuan Xu、Wei Zhang

  DOI：10.1016/j.tet.2011.05.105

  日期：2011.8

  4-Substituted dihydropyrimidinones and dihydropyrimidines were first efficient aerobic oxidized to the corresponding pyrimidinones and pyrimidines, respectively, in high yields by molecular oxygen in the presence of catalytic amount of N-hydroxyphthalimide (NHPI) and Co(OAc)(2) in a mild and environmental benign condition. (C) 2011 Elsevier Ltd. All rights reserved.