1-(2-phenylethyl)-5,6-dihydro-4H-indol-7-one | 1393348-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-phenylethyl)-5,6-dihydro-4H-indol-7-one
• CAS: 1393348-03-2
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: BZGPCAIWFIVJQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  1,2-环己二酮 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 生成 1-(2-phenylethyl)-5,6-dihydro-4H-indol-7-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