1-diphenylacetyl-2-(1-naphthyl)methoxycarbonyloxy-3-phenylindole | 1094901-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-diphenylacetyl-2-(1-naphthyl)methoxycarbonyloxy-3-phenylindole
• CAS: 1094901-09-3
• 化学式: C₄₀H₂₉NO₄
• 分子量: 587.675
• InChiKey: TYXWYFANWAOSMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-diphenylacetyl-2-(1-naphthyl)methoxycarbonyloxy-3-phenylindole 在 2-benzoylamino-1-(4-dimethylaminopyridin-3-yl)-3,3-dimethylbutyl benzyl ether 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以97%的产率得到1-diphenylacetyl-3-(1-naphthyl)methoxycarbonyl-3-phenyloxindole
  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
• 作为产物：
  描述：

  1-diphenylacetyl-3-phenyloxindole 、 1-naphthylmethyl chloroformate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到1-diphenylacetyl-2-(1-naphthyl)methoxycarbonyloxy-3-phenylindole
  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