1,3-dimethyl-3-(prop-1-en-2-yl)indolin-2-one | 1174749-52-0

• 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: 1,3-dimethyl-3-(prop-1-en-2-yl)indolin-2-one
• 英文别名: (3S)-1,3-dimethyl-3-prop-1-en-2-ylindol-2-one
• CAS: 1174749-52-0
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: MUQFVCRQXMOEDL-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-3-(prop-1-en-2-yl)indolin-2-one 在 palladium-on-charcoal 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以89%的产率得到(S)-3-isopropyl-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand

  摘要：

  The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.

  DOI：

  10.1021/ja903880q
• 作为产物：
  描述：

  1,3-二甲基-1,3-二氢-2H-吲哚-2-酮 、 2-溴丙烯 在 [PdMe₂(N,N,N’,N’-tetramethylethylenediamine)] 、 C₃₂H₃₂NP 、 sodium t-butanolate 作用下， 以 环己烷 为溶剂， 反应 24.0h， 以64%的产率得到1,3-dimethyl-3-(prop-1-en-2-yl)indolin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand

  摘要：

  The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.

  DOI：

  10.1021/ja903880q

文献信息

• Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand
  作者：Alexander M. Taylor、Ryan A. Altman、Stephen L. Buchwald

  DOI：10.1021/ja903880q

  日期：2009.7.29

  The enantioselective alpha-arylation and alpha-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are formed in high enantiomeric excess and the conditions tolerate a range of substitution on both the oxindole and the aryl/vinyl coupling partners.