4-methyl-1-tosyl-1H-indole-3-carbaldehyde | 858101-82-3

• 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: 4-methyl-1-tosyl-1H-indole-3-carbaldehyde
• CAS: 858101-82-3
• 化学式: C₁₇H₁₅NO₃S
• 分子量: 313.377
• InChiKey: ZSHMKVZRRSRUJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-methyl-1-tosyl-1H-indole-3-carbaldehyde 在 (R)-trans-Cl₂Ru(pybox-ip)(CH₂=CH₂) 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 cis-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

  DOI：

  10.1021/ol050790n
• 作为产物：
  描述：

  4-甲基吲哚-3-甲醛 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-methyl-1-tosyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  抗真菌剂。第5部分：N-芳基磺酰基-3-酰基吲哚美元的氨基胍衍生物的合成和抗真菌活性

  摘要：

  为了发现更多有希望的抗真菌剂，制备了一系列N-芳基磺酰基-3-酰基林多酚（5a - r）的氨基胍衍生物，并在体外评估了其对7种植物病原真菌的抗真菌活性。尤其是化合物5n和5o表现出比Hymexazol更强的抗真菌活性，Hymexazol是浓度为100μg/ mL的市售农业杀菌剂。初步的结构-活性关系研究表明，引入了给电子性取代基R 1和R 2以及适当长度的取代基R 3 通常对于它们的抗真菌活性非常重要。

  DOI：

  10.1016/j.bmcl.2010.10.084

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.
• Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[<i>b</i>]indoles
  作者：Weiwei Zi、Hongmiao Wu、F. Dean Toste

  DOI：10.1021/jacs.5b00613

  日期：2015.3.11

  A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.