2-(fluoromethyl)-3-phenyl-1-tosyl-1H-indole | 1394401-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(fluoromethyl)-3-phenyl-1-tosyl-1H-indole
• 英文别名: 2-(Fluoromethyl)-1-(4-methylphenyl)sulfonyl-3-phenylindole；2-(fluoromethyl)-1-(4-methylphenyl)sulfonyl-3-phenylindole
• CAS: 1394401-87-6
• 化学式: C₂₂H₁₈FNO₂S
• 分子量: 379.455
• InChiKey: YRSKCSWEFHQVSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-phenyl-1-(2-(tosylamino)phenyl)prop-2-yn-1-ol 在 二乙胺基三氟化硫 、 silver(I) acetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成 2-(fluoromethyl)-3-phenyl-1-tosyl-1H-indole
  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.