N-(7a-methylspiro[5,7-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-6,1'-cyclohexane]-3-ylidene)-4-methylbenzenesulfonamide | 1236286-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: N-(7a-methylspiro[5,7-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-6,1'-cyclohexane]-3-ylidene)-4-methylbenzenesulfonamide
• CAS: 1236286-49-9
• 化学式: C₁₉H₂₆N₂O₃S
• 分子量: 362.493
• InChiKey: QPJKOEHVFCCXET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-((1-(2-methylallyl)cyclohexyl)methylcarbamoyl)-p-toluenesulfonamide 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以95%的产率得到N-(7a-methylspiro[5,7-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-6,1'-cyclohexane]-3-ylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Intramolecular diamination and alkoxyamination of alkenes with N-sulfonyl ureas employing N-iodosuccinimide

  摘要：

  Reaction of N-delta-alkenyl-N'-sulfonyl urea 1 with N-iodosuccinimde (NIS; 2 equiv) and a catalytic amount of AgOTf (20 mol %) at room temperature led to intramolecular alkoxyamination to form bicyclic isourea 2a in 95% isolated yield. In comparison, reaction of 1 with NIS and sodium bicarbonate (1 equiv) at room temperature led to isolation of bicyclic imidazolidin-2-one 2b in 91% yield. These NIS-mediated alkoxyamination and diamination protocols were effective for a range of N-delta-alkenyl-N'-sulfonyl ureas to form the corresponding heterobicyclic compounds in good yield with high chemoselectivity and good to excellent diastereoselectivity. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.03.082

文献信息

• Intramolecular diamination and alkoxyamination of alkenes with N-sulfonyl ureas employing N-iodosuccinimide
  作者：Hao Li、Ross A. Widenhoefer

  DOI：10.1016/j.tet.2010.03.082

  日期：2010.6

  Reaction of N-delta-alkenyl-N'-sulfonyl urea 1 with N-iodosuccinimde (NIS; 2 equiv) and a catalytic amount of AgOTf (20 mol %) at room temperature led to intramolecular alkoxyamination to form bicyclic isourea 2a in 95% isolated yield. In comparison, reaction of 1 with NIS and sodium bicarbonate (1 equiv) at room temperature led to isolation of bicyclic imidazolidin-2-one 2b in 91% yield. These NIS-mediated alkoxyamination and diamination protocols were effective for a range of N-delta-alkenyl-N'-sulfonyl ureas to form the corresponding heterobicyclic compounds in good yield with high chemoselectivity and good to excellent diastereoselectivity. (C) 2010 Published by Elsevier Ltd.