6-benzyl-11-methyl-6H-indolo[2,3-b]quinoline | 1351557-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-benzyl-11-methyl-6H-indolo[2,3-b]quinoline
• 英文别名: 6-Benzyl-11-methylindolo[2,3-b]quinoline
• CAS: 1351557-16-8
• 化学式: C₂₃H₁₈N₂
• 分子量: 322.409
• InChiKey: WXIPUCCDGBEKSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-benzyl-11-methyl-6H-indolo[2,3-b]quinoline 在 aluminum (III) chloride 、 盐酸 作用下， 以 苯 、 水 为溶剂， 反应 9.0h， 以99%的产率得到11-methyl-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered Cross-Amination/Friedel–Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl)ketones

  摘要：

  Activation of C2 and C3 of indoles by molecular iodine (I-2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis. of neocryptolepine and its 11-methyl analogue.

  DOI：

  10.1021/jo202035p
• 作为产物：
  描述：

  1-苄基吲哚 、 N-(2-acetylphenyl)-4-methylbenzenesulfonamide 在 碘 、 caesium carbonate 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 15.0h， 以81%的产率得到6-benzyl-11-methyl-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered Cross-Amination/Friedel–Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl)ketones

  摘要：

  Activation of C2 and C3 of indoles by molecular iodine (I-2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis. of neocryptolepine and its 11-methyl analogue.

  DOI：

  10.1021/jo202035p

文献信息

• One-Pot Access to Indolo[2,3-<i>b</i>]quinolines by Electrophile-Triggered Cross-Amination/Friedel–Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl)ketones
  作者：Shaukat Ali、Ying-Xiu Li、Saeed Anwar、Fang Yang、Zi-Sheng Chen、Yong-Min Liang

  DOI：10.1021/jo202035p

  日期：2012.1.6

  Activation of C2 and C3 of indoles by molecular iodine (I-2) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis. of neocryptolepine and its 11-methyl analogue.