(R)-ethyl 3-(1-(tert-butyldimethylsilyl)-2-oxopropyl)-7-methyl-2-oxoindoline-3-carboxylate | 1373340-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-ethyl 3-(1-(tert-butyldimethylsilyl)-2-oxopropyl)-7-methyl-2-oxoindoline-3-carboxylate
• 英文别名: ethyl (3R)-3-[1-[tert-butyl(dimethyl)silyl]-2-oxopropyl]-7-methyl-2-oxo-1H-indole-3-carboxylate
• CAS: 1373340-49-8
• 化学式: C₂₁H₃₁NO₄Si
• 分子量: 389.567
• InChiKey: CEHYVJASDDKMCJ-FBLFFUNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 3-(1-(tert-butyldimethylsilyl)-2-oxopropyl)-7-methyl-2-oxoindoline-3-carboxylate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到
  参考文献：
  名称：

  Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones

  摘要：

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.

  DOI：

  10.1021/jo302039n
• 作为产物：
  描述：

  (R)-ethyl 3-(1-(tert-butyldimethylsilyl)propa-1,2-dien-1-yl)-7-methyl-2-oxoindoline-3-carboxylate 在 mercury(II) trifluoroacetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.75h， 以72%的产率得到(R)-ethyl 3-(1-(tert-butyldimethylsilyl)-2-oxopropyl)-7-methyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones

  摘要：

  In this Article, a strategy to obtain highly enantio-selective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.

  DOI：

  10.1021/jo302039n