(3R,6S,11aR)-6-ethyl-11a-methyl-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[2,3-b][3]benzazepin-5(6H)-one | 1340590-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (3R,6S,11aR)-6-ethyl-11a-methyl-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[2,3-b][3]benzazepin-5(6H)-one
• CAS: 1340590-08-0
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: HHRMLVOUXWHQNT-HFSMHLIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3R,6S,11aR)-6-ethyl-11a-methyl-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[2,3-b][3]benzazepin-5(6H)-one 在 盐酸 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (1S,4S)-1-ethyl-4-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  Asymmetric synthesis of enantiomerically pure 1,4-di- and 1,1,4-trisubstituted tetrahydro-1H-3-benzazepines

  摘要：

  A four step asymmetric synthesis of 1,4-di- and 1,1,4-trisubstituted enantiomerically pure tetrahydro-3-benzazepines is described. Tricyclic oxazolobenzazepinones trans-9 and cis-10 allow the introduction of different alkyl groups (methyl, ethyl, allyl) with high diastereoselectivity (dr > 99:1). The relative configuration of the new stereogenic center was determined by NOE experiments. Tricyclic lactams trans-9 and cis-10 were also used for the introduction of two substituents and, moreover, the establishment of spiro-cyclic rings. Reduction of the substitution products 11 and 12 with AlCl3/LiAlH4 (1:3) took place with retention of configuration and the final hydrogenolytic removal of the N-(2-hydroxy-1-phenylethyl) residue provided enantiomerically pure 1,4-di- and 1,1,4-trisubstituted tetrahydro-3-benzazepines 17 and ent-17. In receptor binding studies with radioligands, the 3-benzazepines 17a-g and ent-17a-g did not show any interactions with cri, sigma(1), sigma(2) or NMDA receptors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.027
• 作为产物：
  描述：

  D-苯甘氨醇 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (3R,6S,11aR)-6-ethyl-11a-methyl-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 enantiomerically pure 1,4-di- and 1,1,4-trisubstituted tetrahydro-1H-3-benzazepines

  摘要：

  A four step asymmetric synthesis of 1,4-di- and 1,1,4-trisubstituted enantiomerically pure tetrahydro-3-benzazepines is described. Tricyclic oxazolobenzazepinones trans-9 and cis-10 allow the introduction of different alkyl groups (methyl, ethyl, allyl) with high diastereoselectivity (dr > 99:1). The relative configuration of the new stereogenic center was determined by NOE experiments. Tricyclic lactams trans-9 and cis-10 were also used for the introduction of two substituents and, moreover, the establishment of spiro-cyclic rings. Reduction of the substitution products 11 and 12 with AlCl3/LiAlH4 (1:3) took place with retention of configuration and the final hydrogenolytic removal of the N-(2-hydroxy-1-phenylethyl) residue provided enantiomerically pure 1,4-di- and 1,1,4-trisubstituted tetrahydro-3-benzazepines 17 and ent-17. In receptor binding studies with radioligands, the 3-benzazepines 17a-g and ent-17a-g did not show any interactions with cri, sigma(1), sigma(2) or NMDA receptors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.027