N-(2-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)methanesulfonamide | 1394401-61-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(2-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)methanesulfonamide
• 英文别名: N-[2-(1-hydroxy-1,3-diphenylprop-2-ynyl)phenyl]methanesulfonamide
• CAS: 1394401-61-6
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: CKXVEKWREFVVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)methanesulfonamide 在 silver(I) acetate 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以99%的产率得到(Z)-2-benzylidene-1-(methylsulfonyl)-3-phenylindolin-3-ol
  参考文献：
  名称：

  Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols

  摘要：

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

  DOI：

  10.1021/jo301198z
• 作为产物：
  描述：

  2-氨基二苯甲酮 在 吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 1.42h， 生成 N-(2-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)methanesulfonamide
  参考文献：
  名称：

  Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols

  摘要：

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

  DOI：

  10.1021/jo301198z

文献信息

• Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (<i>Z</i>)<i>-</i>2-Methylene-1-sulfonylindolin-3-ols
  作者：Dewi Susanti、Fujiet Koh、Jeffrey Antonius Kusuma、Prasath Kothandaraman、Philip Wai Hong Chan

  DOI：10.1021/jo301198z

  日期：2012.9.7

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.