(1R,4R)-1,4-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine

• 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: (1R,4R)-1,4-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: (2R,5R)-2,5-dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: AFYVRKZGMCHHIY-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2-(2-oxopropyl)phenyl)acetic acid 在 盐酸 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 (1R,4R)-1,4-dimethyl-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

文献信息

• Asymmetric synthesis of enantiomerically pure 1,4-di- and 1,1,4-trisubstituted tetrahydro-1H-3-benzazepines
  作者：Soumya Sarkar、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.tetasy.2011.07.027

  日期：2011.7

  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.