(2S,3R)-2-benzyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal | 1417616-11-5

• 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-benzyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butanal
• 英文别名: (2S,3R)-2-benzyl-3-[1-(4-methylphenyl)sulfonylindol-3-yl]-4-nitrobutanal
• CAS: 1417616-11-5
• 化学式: C₂₆H₂₄N₂O₅S
• 分子量: 476.553
• InChiKey: ADZNRDBGMZBPNJ-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 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 67.0h， 生成 (2S,3R)-2-benzyl-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

• Hybrid Peptide–Thiourea Catalyst for Asymmetric Michael Additions of Aldehydes to Heterocyclic Nitroalkenes
  作者：Patrícia Čmelová、Denisa Vargová、Radovan Šebesta

  DOI：10.1021/acs.joc.0c02251

  日期：2021.1.1

  noncovalent activation is presented. The hybrid peptide–thiourea catalyst features a N-terminal proline moiety for aldehyde activation and a thiourea unit for electrophile activation. This catalyst effectively promotes asymmetric Michael additions of aldehydes to challenging but biologically relevant heterocycle-containing nitroalkenes. The catalyst can be used under solvent-free conditions. Spectroscopic

  提出了结合共价和非共价活化的双功能有机催化。杂肽-硫脲催化剂具有用于醛活化的N末端脯氨酸部分和用于亲电试剂活化的硫脲单元。该催化剂有效地促进醛向具有挑战性但生物学上相关的含杂环硝基烯烃的醛的不对称迈克尔加成。该催化剂可以在无溶剂的条件下使用。光谱和密度泛函理论研究阐明了催化剂的结构和作用方式。
• 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.