5-acetyl-4-(trichloro-methyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one | 1210056-72-6

• 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: 5-acetyl-4-(trichloro-methyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one
• 英文别名: 5-acetyl-6-methyl-4-(trichloromethyl)-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 1210056-72-6
• 化学式: C₈H₉Cl₃N₂O₂
• 分子量: 271.531
• InChiKey: YSRFTUJRULKDKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-4-(trichloro-methyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.2h， 以72%的产率得到4-甲基-5-乙酰基嘧啶2-酮
  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-[(3-acetyl-1,1,1-trichloro-4-oxo)pent-2-yl]urea 在 对甲苯磺酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.6h， 以94.9%的产率得到5-acetyl-4-(trichloro-methyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-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

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.