2-[2-(2,2-Dimethoxy-ethyl)-phenyl]-N-((R)-1-phenyl-2-triisopropylsilanyloxy-ethyl)-acetamide | 863908-20-7

• 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: 2-[2-(2,2-Dimethoxy-ethyl)-phenyl]-N-((R)-1-phenyl-2-triisopropylsilanyloxy-ethyl)-acetamide
• CAS: 863908-20-7
• 化学式: C₂₉H₄₅NO₄Si
• 分子量: 499.766
• InChiKey: IJUJMKYSBWAXSW-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[2-(2,2-Dimethoxy-ethyl)-phenyl]-N-((R)-1-phenyl-2-triisopropylsilanyloxy-ethyl)-acetamide 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 9.0h， 生成 (3R,6R,11aS)-6-benzyl-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[2,3-b][3]benzazepin-5(6H)-one
  参考文献：
  名称：

  Asymmetric synthesis of 1-substituted tetrahydro-3-benzoazepines

  摘要：

  In order to develop a new asymmetric synthesis of enantiomerically pure 1-substituted tetrahydro-3-benzoazepines 3, the synthesis of diastereomerically pure oxazolo[3]benzoazepin one 4 has been performed. The stereochemical information of the key intermediate 4 originates from the chiral auxiliary (R)-phenylglycinol. The tricyclic ring system of 4 allows the stereoselective introduction of a benzyl residue at the 6-position to obtain benzyl derivative 15 with a diastereoselectivity of 95.1:4.9. The relative configuration of the main product 15 was determined by X-ray crystal structure analysis. Reductive degradation of diastereomerically pure 15 led to enantiomerically pure (R)-1-benzyl-3-benzoazepine 17. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.007
• 作为产物：
  描述：

  methyl (R)-2-{2-[N-(2-hydroxy-1-phenylethyl)carbamoylmethyl]phenyl}acetate 在 咪唑 、 盐酸 、 锂硼氢 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 2-[2-(2,2-Dimethoxy-ethyl)-phenyl]-N-((R)-1-phenyl-2-triisopropylsilanyloxy-ethyl)-acetamide
  参考文献：
  名称：

  Asymmetric synthesis of 1-substituted tetrahydro-3-benzoazepines

  摘要：

  In order to develop a new asymmetric synthesis of enantiomerically pure 1-substituted tetrahydro-3-benzoazepines 3, the synthesis of diastereomerically pure oxazolo[3]benzoazepin one 4 has been performed. The stereochemical information of the key intermediate 4 originates from the chiral auxiliary (R)-phenylglycinol. The tricyclic ring system of 4 allows the stereoselective introduction of a benzyl residue at the 6-position to obtain benzyl derivative 15 with a diastereoselectivity of 95.1:4.9. The relative configuration of the main product 15 was determined by X-ray crystal structure analysis. Reductive degradation of diastereomerically pure 15 led to enantiomerically pure (R)-1-benzyl-3-benzoazepine 17. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.007