4-(trichloromethyl)-6-phenyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one | 1245640-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(trichloromethyl)-6-phenyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one
• CAS: 1245640-33-8
• 化学式: C₁₈H₁₅Cl₃N₂O₃S
• 分子量: 445.754
• InChiKey: OKJBYZCKVWQYSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(trichloromethyl)-6-phenyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one 在 sodium hydride 作用下， 以 乙腈 、 mineral oil 为溶剂， 反应 1.67h， 以79.6%的产率得到4-phenyl-5-tosyl-1,2-dihydropyrimidin-2-one
  参考文献：
  名称：

  New approach to 5-arylsulfonyl-substituted 1,2-dihydropyrimidin-2-ones via base-induced chloroform elimination from 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A four-step method for the synthesis of 5-arylsulfonyl-substituted 1,2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2,2,2-trichloro)ethyl]ureas with sodium enolates of alpha-arylsulfonylketones followed by heterocyclization dehydration of the oxoalkylureas formed gave 5-arylsulfonyl-4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. The latter, in the presence of strong bases, eliminate CHCl3 to give the target compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.058
• 作为产物：
  描述：

  (2RS,3SR)-N-acetyl-N'-[(1,1,1-trichloro-4-oxo-4-phenyl-3-tosyl)but-2-yl]urea 在 对甲苯磺酸 作用下， 以 正丁醇 为溶剂， 反应 18.0h， 以72%的产率得到4-(trichloromethyl)-6-phenyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one
  参考文献：
  名称：

  New approach to 5-arylsulfonyl-substituted 1,2-dihydropyrimidin-2-ones via base-induced chloroform elimination from 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones

  摘要：

  A four-step method for the synthesis of 5-arylsulfonyl-substituted 1,2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2,2,2-trichloro)ethyl]ureas with sodium enolates of alpha-arylsulfonylketones followed by heterocyclization dehydration of the oxoalkylureas formed gave 5-arylsulfonyl-4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. The latter, in the presence of strong bases, eliminate CHCl3 to give the target compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.058