3-amino-2-(6-bromo-1H-indol-4-yl)cyclohex-2-en-1-one | 1271141-88-8

• 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: 3-amino-2-(6-bromo-1H-indol-4-yl)cyclohex-2-en-1-one
• CAS: 1271141-88-8
• 化学式: C₁₄H₁₃BrN₂O
• 分子量: 305.174
• InChiKey: OEHQDSQKRXGYFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(triisopropylsilyl)-1H-indol-5-ol 在 四甲基乙二胺 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二乙胺 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 、 正戊烷 为溶剂， 反应 45.86h， 生成 3-amino-2-(6-bromo-1H-indol-4-yl)cyclohex-2-en-1-one 、 3-amino-2-(6-bromo-1H-indol-5-yl)cyclohex-2-en-1-one
  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.