N-[(3-acetyl-1,1,1-trichloro-4-oxo)pent-2-yl]urea | 1210056-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(3-acetyl-1,1,1-trichloro-4-oxo)pent-2-yl]urea
• 英文别名: (3-Acetyl-1,1,1-trichloro-4-oxopentan-2-yl)urea
• CAS: 1210056-66-8
• 化学式: C₈H₁₁Cl₃N₂O₃
• 分子量: 289.546
• InChiKey: PJGALOSBDSFAIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(3-acetyl-1,1,1-trichloro-4-oxo)pent-2-yl]urea 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以72.9%的产率得到(4RS,6SR)-6-(trichloro-methyl)-4-hydroxy-4-methylhexahydropyrimidin-2-one
  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 、 乙酰丙酮 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 3.6h， 以70%的产率得到N-[(3-acetyl-1,1,1-trichloro-4-oxo)pent-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.