N-[(1-benzoyloxy-4-oxo-4-phenyl-3-tosyl)but-2-yl]urea | 1332329-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1-benzoyloxy-4-oxo-4-phenyl-3-tosyl)but-2-yl]urea
• CAS: 1332329-74-4
• 化学式: C₂₅H₂₄N₂O₆S
• 分子量: 480.541
• InChiKey: KYFFVODXYYSUES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  132.63
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(1-benzoyloxy-4-oxo-4-phenyl-3-tosyl)but-2-yl]urea 在 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 22.82h， 生成 4-(mesyloxymethyl)-6-phenyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one
  参考文献：
  名称：

  Nucleophile-mediated ring expansion of 4-chloromethyl- and 4-mesyloxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones to 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones: effect of the leaving group and the substituent at C6

  摘要：

  A five-step synthesis of 4-chloromethyl- and 4-mesyloxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones has been developed. The reaction of N-[(2-benzoyloxy-1-tosyl)ethyl]urea with sodium enolates of alpha-tosylketones followed by cyclization-dehydration, and debenzoylation gave 4-hydroxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones, which were transformed into the 4-chloromethyl- or 4-mesyloxymethyl-derivatives. Treatment of the latter with nucleophilic reagents, such as sodium cyanide, sodium diethyl malonate, sodium thiophenolate, or potassium phthalimide, afforded the corresponding 4,7-disubstituted 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones as a result of ring expansion. The effect of the leaving group and the substitution at the position C6 on the reactivity of the pyrimidines is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.089
• 作为产物：
  描述：

  Α-(对甲苯磺酰)苯乙酮 、 N-[(2-benzoyloxy-1-tosyl)ethyl]urea 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 8.27h， 以96%的产率得到N-[(1-benzoyloxy-4-oxo-4-phenyl-3-tosyl)but-2-yl]urea
  参考文献：
  名称：

  Nucleophile-mediated ring expansion of 4-chloromethyl- and 4-mesyloxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones to 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones: effect of the leaving group and the substituent at C6

  摘要：

  A five-step synthesis of 4-chloromethyl- and 4-mesyloxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones has been developed. The reaction of N-[(2-benzoyloxy-1-tosyl)ethyl]urea with sodium enolates of alpha-tosylketones followed by cyclization-dehydration, and debenzoylation gave 4-hydroxymethyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-ones, which were transformed into the 4-chloromethyl- or 4-mesyloxymethyl-derivatives. Treatment of the latter with nucleophilic reagents, such as sodium cyanide, sodium diethyl malonate, sodium thiophenolate, or potassium phthalimide, afforded the corresponding 4,7-disubstituted 6-tosyl-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones as a result of ring expansion. The effect of the leaving group and the substitution at the position C6 on the reactivity of the pyrimidines is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.089