ethyl 3-(1-acetyl-6-fluoro-1H-indol-2-yl)propanoate | 1403485-78-8

• 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: ethyl 3-(1-acetyl-6-fluoro-1H-indol-2-yl)propanoate
• 英文别名: Ethyl 3-(1-acetyl-6-fluoroindol-2-yl)propanoate；ethyl 3-(1-acetyl-6-fluoroindol-2-yl)propanoate
• CAS: 1403485-78-8
• 化学式: C₁₅H₁₆FNO₃
• 分子量: 277.295
• InChiKey: NJNNCKKEDZETDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-氟吲哚 在 (1Z,5Z)-cycloocta-1,5-diene,iridium,tetrafluoroborate 、 四丁基硫酸氢铵 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl 3-(1-acetyl-6-fluoro-1H-indol-2-yl)propanoate
  参考文献：
  名称：

  Ir(I)-Catalyzed C–H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles

  摘要：

  A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

  DOI：

  10.1021/ja308742x

文献信息

• Ir(I)-Catalyzed C–H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles
  作者：Shiguang Pan、Naoto Ryu、Takanori Shibata

  DOI：10.1021/ja308742x

  日期：2012.10.24

  A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.