1-benzyl-2-ethyl-3-methyl-1H-indole

• 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: 1-benzyl-2-ethyl-3-methyl-1H-indole
• 英文别名: 1-benzyl-2-ethyl-3-methylindole
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: ZJMXWEZNMKLPOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-Benzyl-N'-(1-ethyl-propylidene)-N-phenyl-hydrazine 在 diethyl(2,2,6,6-tetramethylpiperidino)aluminium 作用下， 以74%的产率得到1-benzyl-2-ethyl-3-methyl-1H-indole
  参考文献：
  名称：

  Regioselective Fischer indole synthesis mediated by organoaluminum amides

  摘要：

  Amphiphilic reagents such as organoaluminum amides are found to be highly effective for the Fischer indole synthesis. In particular, diethylaluminum 2,2,6,6-tetramethylpiperidide (DATMP) is the reagent of choice for regioselective Fischer indole synthesis. For example, treatment of the (E)-N-methyl-N-phenylhydrazone of 5-methyl-3-heptanone with DATMP affords 3-sec-butyl-2-ethyl-1-methylindole as the sole isolable product; its Z-isomer affords 1,3-dimethyl-2-(2-methylbutyl)indole with high regioselectivity under similar reaction conditions.

  DOI：

  10.1021/jo00079a005

文献信息

• Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins
  作者：Xiaowei Dou、Weijun Yao、Shan Wen、Yixin Lu

  DOI：10.1039/c4cc04555f

  日期：——

  A facile regiospecific synthesis of 2,3-disubstituted indoles from isatins has been developed. Nucleophilic addition of Grignard reagents to commercially available isatins, followed by reduction with borane, afforded an array of structurally diverse 2,3-disubstituted indoles in moderate to good yields. The method described herein represents a novel and very simple approach to synthesize various 2,3-disubstituted

  已经开发了从靛红容易地区域特异性合成2，3-二取代的吲哚的方法。将格氏试剂亲核地添加到市售的靛红中，然后用硼烷还原，以中等至良好的产率提供了结构上不同的2，3-二取代的吲哚阵列。本文所述的方法代表了一种新颖且非常简单的方法，用于合成各种2，3-二取代的吲哚，这是制药工业和药物化学中极为重要的结构基序。
• 10.1055/s-0043-1775363
  作者：Sugimoto, Kenji、Wada, Yusei、Kitamura, Fumino、Matsuya, Yuji

  DOI：10.1055/s-0043-1775363

  日期：——

  AbstractAn organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.y
• Regioselective Fischer indole synthesis mediated by organoaluminum amides
  作者：Keiji Maruoka、Masataka Oishi、Hisashi Yamamoto

  DOI：10.1021/jo00079a005

  日期：1993.12

  Amphiphilic reagents such as organoaluminum amides are found to be highly effective for the Fischer indole synthesis. In particular, diethylaluminum 2,2,6,6-tetramethylpiperidide (DATMP) is the reagent of choice for regioselective Fischer indole synthesis. For example, treatment of the (E)-N-methyl-N-phenylhydrazone of 5-methyl-3-heptanone with DATMP affords 3-sec-butyl-2-ethyl-1-methylindole as the sole isolable product; its Z-isomer affords 1,3-dimethyl-2-(2-methylbutyl)indole with high regioselectivity under similar reaction conditions.