5-bromo-1-(4-methylphenyl)sulfonyl-3-[(E)-2-nitroethenyl]indole | 1417616-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-1-(4-methylphenyl)sulfonyl-3-[(E)-2-nitroethenyl]indole
• CAS: 1417616-00-2
• 化学式: C₁₇H₁₃BrN₂O₄S
• 分子量: 421.271
• InChiKey: YEIFAPUUMJFWJZ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  庚醛 、 5-bromo-1-(4-methylphenyl)sulfonyl-3-[(E)-2-nitroethenyl]indole 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以95%的产率得到(S)-2-((R)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-heptanal
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors

  摘要：

  Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1-ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.

  DOI：

  10.1021/jo3024945
• 作为产物：
  描述：

  5-溴吲哚 在 ammonium acetate 、 三氯氧磷 作用下， 生成 5-bromo-1-(4-methylphenyl)sulfonyl-3-[(E)-2-nitroethenyl]indole
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors

  摘要：

  Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1-ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.

  DOI：

  10.1021/jo3024945