6-bromo-N-phenyl-1H-indol-4-amine | 1271141-76-4

• 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: 6-bromo-N-phenyl-1H-indol-4-amine
• CAS: 1271141-76-4
• 化学式: C₁₄H₁₁BrN₂
• 分子量: 287.159
• InChiKey: BXCGSWMMKSUCGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-bromo-1-(triisopropylsilyl)-4-(trimethylsilyl)-1H-indol-5-yl isopropylcarbamate 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.97h， 生成 6-bromo-N-phenyl-1H-indol-4-amine 、 6-bromo-N-phenyl-1H-indol-5-amine
  参考文献：
  名称：

  Overturning Indolyne Regioselectivities and Synthesis of Indolactam V

  摘要：

  We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.

  DOI：

  10.1021/ja200437g

文献信息

• Overturning Indolyne Regioselectivities and Synthesis of Indolactam V
  作者：Sarah M. Bronner、Adam E. Goetz、Neil K. Garg

  DOI：10.1021/ja200437g

  日期：2011.3.23

  We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.