(2S,3R)-2-ethyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal | 1417616-07-9

• 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: (2S,3R)-2-ethyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal
• 英文别名: (2S,3R)-2-ethyl-3-[1-(4-methylphenyl)sulfonylindol-3-yl]-4-nitrobutanal
• CAS: 1417616-07-9
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: DIJNYWAYGVXYGY-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2S,3R)-2-ethyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal 在 sodium tetrahydroborate 、 10 mol% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 36.0h， 以74%的产率得到tert-butyl (2R,3S)-3-(hydroxymethyl)-2-(1H-indol-3-yl)pentylcarbamate
  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：

  1-[(4-甲基苯基)磺酰]-1H-吲哚-3-甲醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 ammonium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S,3R)-2-ethyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal
  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

文献信息

• Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors
  作者：Jian Chen、Zhi-Cong Geng、Ning Li、Xiao-Fei Huang、Feng-Feng Pan、Xing-Wang Wang

  DOI：10.1021/jo3024945

  日期：2013.3.15

  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.