ethyl (S)-2-(1,2-dimethyl-1H-indol-3-yl)butanoate | 1264995-84-7

• 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: ethyl (S)-2-(1,2-dimethyl-1H-indol-3-yl)butanoate
• 英文别名: ethyl (2S)-2-(1,2-dimethylindol-3-yl)hexanoate
• CAS: 1264995-84-7
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: OKECMRHUDLOZGM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基吲哚 、 ethyl 2-diazohexanoate 在 Rh₂(R-PTAD)₄ 作用下， 以 甲苯 为溶剂， 以54%的产率得到ethyl (S)-2-(1,2-dimethyl-1H-indol-3-yl)butanoate
  参考文献：
  名称：

  Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles

  摘要：

  A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

  DOI：

  10.1021/ja1093309

文献信息

• Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
  作者：Andrew DeAngelis、Valerie W. Shurtleff、Olga Dmitrenko、Joseph M. Fox

  DOI：10.1021/ja1093309

  日期：2011.2.16

  A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.