1-acetyl-3-(2-(tert-Butyldiphenylsilanyloxy)ethyl)-1-diphenylacetyloxindole | 1094900-87-4

• 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: 1-acetyl-3-(2-(tert-Butyldiphenylsilanyloxy)ethyl)-1-diphenylacetyloxindole
• 英文别名: (3S)-3-acetyl-3-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-1-(2,2-diphenylacetyl)indol-2-one
• CAS: 1094900-87-4
• 化学式: C₄₂H₄₁NO₄Si
• 分子量: 651.877
• InChiKey: KGBYYQZNNYHDKQ-HUESYALOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-acetoxy-3-(2-(tert-Butyldiphenylsilanyloxy)ethyl)-1-diphenylacetylindole 在 (1S,2S)-2-benzamido-1-(4-(dimethylamino)pyridin-3-yl)-3,3-dimethylbutyl acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以94%的产率得到1-acetyl-3-(2-(tert-Butyldiphenylsilanyloxy)ethyl)-1-diphenylacetyloxindole
  参考文献：
  名称：

  AcOLeDMAP and BnOLeDMAP: Conformationally Restricted Nucleophilic Catalysts for Enantioselective Rearrangement of Indolyl Acetates and Carbonates

  摘要：

  The rate of indotyl O- to C-acetyl or carboxyl rearrangement is accelerated by the electron-withdrawing N-diphenylacetyl group (DPA) using the conformationally restricted chiral catalysts AcOLeDMAP (12b) and BnOLeDMAP (13b). Highly enantioselective conversion to quaternary C-acetylated and C-carboxylated oxindoles is observed, even for substrates containing branched substituents. The rearrangement of the carboxylate substrates 19 occurs with complementary enantiofacial selectivity using catalyst 13b compared to the acetyl migrations of 16 catalyzed by 12b. Access to N-unsubstituted oxindoles is demonstrated by DPA cleavage with Et2NH.

  DOI：

  10.1021/ja805541u

文献信息

• AcOLeDMAP and BnOLeDMAP: Conformationally Restricted Nucleophilic Catalysts for Enantioselective Rearrangement of Indolyl Acetates and Carbonates
  作者：Trisha A. Duffey、Scott A. Shaw、Edwin Vedejs

  DOI：10.1021/ja805541u

  日期：2009.1.14

  The rate of indotyl O- to C-acetyl or carboxyl rearrangement is accelerated by the electron-withdrawing N-diphenylacetyl group (DPA) using the conformationally restricted chiral catalysts AcOLeDMAP (12b) and BnOLeDMAP (13b). Highly enantioselective conversion to quaternary C-acetylated and C-carboxylated oxindoles is observed, even for substrates containing branched substituents. The rearrangement of the carboxylate substrates 19 occurs with complementary enantiofacial selectivity using catalyst 13b compared to the acetyl migrations of 16 catalyzed by 12b. Access to N-unsubstituted oxindoles is demonstrated by DPA cleavage with Et2NH.