6,7-dihydro-1-phenethyl-1H-indol-4(5H)-one | 1006872-07-6

• 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: 6,7-dihydro-1-phenethyl-1H-indol-4(5H)-one
• 英文别名: 1-(2-phenylethyl)-6,7-dihydro-5H-indol-4-one
• CAS: 1006872-07-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: YNCOXJGIDIBQQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6,7-二氢-4(5H)-苯并呋喃酮 、 2-苯乙胺 以 乙醇 、 水 为溶剂， 反应 12.0h， 以71%的产率得到6,7-dihydro-1-phenethyl-1H-indol-4(5H)-one
  参考文献：
  名称：

  Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles

  摘要：

  An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center a to the nitrogen and preparation of enantiomerically enriched products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.090

文献信息

• Scaffold Preparation and Parallel Synthesis of Arrays of 5,6,7,8-Tetrahydropyrrolo-azepinones in the Solution Phase
  作者：Leonarda Piras、Eva Genesio、Chiara Ghiron、Maurizio Taddei

  DOI：10.1002/ejoc.200701024

  日期：2008.6

  into the corresponding (Z)-oxime which gave the pyrrolo-azepinone by Beckmann rearrangement in the presence of polyphosphoric acid. Trimethylaluminium-mediated amidation gave the corresponding amides which were finally N-alkylated at the 5-position to give 52 diverse (pyrrolo-azepinyl)acetamides, showing an appreciable exploration of the chemical space around the central heterocyclic core. (© Wiley-VCH

  描述了用于平行制备 (oxo-pyrrolo-azepinyl) 乙酰胺阵列的吡咯-氮杂支架的有效合成。1,3-环己二酮与溴丙酮酸乙酯的 Stetter 环化反应是组装四氢苯并呋喃底物的关键反应，该底物在甘氨酸存在下通过微波辅助环缩合反应快速转化为四氢吲哚。然后将羰基立体选择性地转化为相应的 (Z)-肟，在多磷酸存在下通过贝克曼重排得到吡咯并-氮杂。三甲基铝介导的酰胺化得到相应的酰胺，最终在 5 位 N-烷基化得到 52 种不同的（吡咯并氮杂）乙酰胺，显示了对中央杂环核周围化学空间的可观探索。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Microwave-assisted synthesis of tetrahydroindoles
  作者：Leonarda Piras、Chiara Ghiron、Giacomo Minetto、Maurizio Taddei

  DOI：10.1016/j.tetlet.2007.11.114

  日期：2008.1

  An efficient synthesis of tetrahydroindoles with different substituents in position I is described. Microwave-assisted aminolysis of 4-oxo-4,5,6,7-tetrahydrobenzofuran With different primary amines gives the corresponding tetrahydroindoles in few minutes. All attempts to use microwave dielectric heating to reduce the time required for preparation of 4-oxo-4,5,6,7-tetrahydrobenzofuran, starting from 1,3-cyclohexandione were on the other hand unsuccessful, demonstrating that in some cases, long time conventional heating may be superior to microwaves. (C) 2007 Elsevier Ltd. All rights reserved.