(E)-N-(4-cyclohexylbut-3-en-1-yn-1-yl)-N-methylmethanesulfonamide | 1562381-17-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (E)-N-(4-cyclohexylbut-3-en-1-yn-1-yl)-N-methylmethanesulfonamide
• 英文别名: N-[(E)-4-cyclohexylbut-3-en-1-ynyl]-N-methylmethanesulfonamide
• CAS: 1562381-17-2
• 化学式: C₁₂H₁₉NO₂S
• 分子量: 241.354
• InChiKey: NCMQBQSAHNZJLE-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-(4-cyclohexylbut-3-en-1-yn-1-yl)-N-methylmethanesulfonamide 在 三氟甲磺酸三甲基硅酯 、 zinc trifluoromethanesulfonate 、 二异丙胺 、 zinc dibromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 4-hydroxy-N-methyl-N-(methylsulfonyl)-N',4-diphenylbut-2-ynimidamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w
• 作为产物：
  描述：

  4-Cyclohexyl-buten-(3)-in-(1) 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 (E)-N-(4-cyclohexylbut-3-en-1-yn-1-yl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w