ethyl 4-(trichloro-methyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1210056-74-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 4-(trichloro-methyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• CAS: 1210056-74-8
• 化学式: C₁₄H₁₃Cl₃N₂O₃
• 分子量: 363.628
• InChiKey: KOJYKFULIRIHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(trichloro-methyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以69.6%的产率得到2-羟基-4-苯基嘧啶-5-羧酸甲酯
  参考文献：
  名称：

  A novel convenient synthesis of 5-acyl-1,2-dihydropyrimidin-2-ones via 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A novel four-step methodology for the synthesis of 5-acyl-1,2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2,2,2-trichloro)ethyl]ureas with Na-enolates of 1,3-diketones or beta-oxoesters followed by heterocyclization-dehydration of the oxoalkylureas formed gave 5-acyl-4-trichloromethyl-1,2,3,4-tetrahydtopyrimidin-2-ones. The latter, in the presence of NaH, eliminate CHCl3 to give the target compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.099
• 作为产物：
  描述：

  N-[(1,1,1-trichloro-3-ethoxycarbonyl-4-oxo-4-phenyl)but-2-yl]urea 在 对甲苯磺酸 作用下， 以 水 、 乙腈 为溶剂， 反应 14.18h， 以75.2%的产率得到ethyl 4-(trichloro-methyl)-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A novel convenient synthesis of 5-acyl-1,2-dihydropyrimidin-2-ones via 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A novel four-step methodology for the synthesis of 5-acyl-1,2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2,2,2-trichloro)ethyl]ureas with Na-enolates of 1,3-diketones or beta-oxoesters followed by heterocyclization-dehydration of the oxoalkylureas formed gave 5-acyl-4-trichloromethyl-1,2,3,4-tetrahydtopyrimidin-2-ones. The latter, in the presence of NaH, eliminate CHCl3 to give the target compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.099