2,4-bis(4-allyloxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one | 1350856-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,4-bis(4-allyloxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
• CAS: 1350856-66-4
• 化学式: C₂₆H₂₉NO₃
• 分子量: 403.521
• InChiKey: NDBGXBJZIRMAJN-UCDDGIFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-烯丙氧基苯甲醛 、 环己酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 2,4-bis(4-allyloxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
  参考文献：
  名称：

  A complete 1D and 2D NMR studies of variously substituted 3-azabicyclo[3.3.1]nonan-9-ones

  摘要：

  Variously substituted 3-azabicyclo[3.3.1]nonan-9-ones viz, 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones, 2,4-diaryl-1-methyl-3-azabicyclo[3.3.1]nonan-9-ones and 2,4-diaryl-7-methyl-3-azabicyclo[3.3.1]nonan-9-ones were conveniently synthesized by a modified and an optimized one-pot Mannich condensation of cyclohexanones, benzaldehydes and ammonium acetate in 1:2:1.5 M ratio. All the synthesized bicycles were examined by their physical and spectral (IR, HR-MS, (1)H NMR and (13)C NMR) techniques. In order to establish their unambiguous stereochemical assignments, H,H-COSY, HET-COSY, HMBC, NOESY and dynamic NMR investigations have been carried out for some of the representative compounds. The detailed NMR analysis proved that all the synthesized 3-azabicycles exist in a twin-chair conformation with an equatorial orientation of the substituents, regardless the incorporation of either linear or bulkier groups on the phenyl and/or methyl on the heterocycle or carbocycle. The electronic effects of methylation on the azabicycle as well as the ortho substitution on the phenyl provided some useful insights. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.08.006