2-methylene-3-phenyl-1-tosylindolin-3-ol | 1394401-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methylene-3-phenyl-1-tosylindolin-3-ol
• 英文别名: 2-Methylidene-1-(4-methylphenyl)sulfonyl-3-phenylindol-3-ol；2-methylidene-1-(4-methylphenyl)sulfonyl-3-phenylindol-3-ol
• CAS: 1394401-78-5
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: WKSVERVCHTYKJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylene-3-phenyl-1-tosylindolin-3-ol 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以87%的产率得到3-(iodomethyl)-3-phenyl-1-tosylindolin-2-one
  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：

  1-phenyl-1-(2-(tosylamino)phenyl)prop-2-yn-1-ol 在 silver(I) acetate 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以87%的产率得到2-methylene-3-phenyl-1-tosylindolin-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

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.
• Synergistic Gold and Iron Dual Catalysis: Preferred Radical Addition toward Vinyl–Gold Intermediate over Alkene
  作者：Haihui Peng、Novruz G. Akhmedov、Yu-Feng Liang、Ning Jiao、Xiaodong Shi

  DOI：10.1021/jacs.5b05415

  日期：2015.7.22

  A dual catalytic approach enlisting gold and iron, synergy is described. This method offers readily access to substituted heterocycle aldehydes via oxygen radical addition to vinyl-gold intermediates under Fe catalyst assistance. This system shows good functional group compatibility for the generation of substituted oxazole, indole, and benzofuran aldehydes. Mechanistic evidence greatly supports selective radical addition to an: activated vinyl-Au double bond over alkene. This unique discovery offers a new avenue with great potential to further extend the synthetic power and versatility of gold catalysis.