N-[(1,1,1-trichloro-3-ethoxycarbonyl-4-oxo-4-phenyl)but-2-yl]urea | 1210056-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1,1,1-trichloro-3-ethoxycarbonyl-4-oxo-4-phenyl)but-2-yl]urea
• 英文别名: Ethyl 2-benzoyl-3-(carbamoylamino)-4,4,4-trichlorobutanoate；ethyl 2-benzoyl-3-(carbamoylamino)-4,4,4-trichlorobutanoate
• CAS: 1210056-69-1
• 化学式: C₁₄H₁₅Cl₃N₂O₄
• 分子量: 381.643
• InChiKey: BUUFZMGZHKBEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-[(1-acetoxy-2,2,2-trichloro)ethyl]urea 、 苯甲酰乙酸乙酯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 0.27h， 以94.5%的产率得到N-[(1,1,1-trichloro-3-ethoxycarbonyl-4-oxo-4-phenyl)but-2-yl]urea
  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

文献信息

• A novel convenient synthesis of 5-acyl-1,2-dihydropyrimidin-2-ones via 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones
  作者：Anastasia A. Fesenko、Pavel A. Solovyev、Anatoly D. Shutalev

  DOI：10.1016/j.tet.2009.11.099

  日期：2010.1

  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.