(S)-7-chloro-5-methoxymethyloxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine | 331947-57-0

• 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: (S)-7-chloro-5-methoxymethyloxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: N-[4-[(5S)-7-chloro-5-(methoxymethoxy)-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl]-3-methylphenyl]-2-methylbenzamide
• CAS: 331947-57-0
• 化学式: C₂₈H₂₉ClN₂O₄
• 分子量: 493.002
• InChiKey: XRKUBDGJBZWQAI-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-7-chloro-5-methoxymethyloxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以74%的产率得到(S)-(-)-托伐普坦
  参考文献：
  名称：

  An Efficient Synthesis of Optical Isomers of Vasopressin V2 Receptor Antagonist OPC-41061 by Lipase-catalyzed Enantioselective Transesterification

  摘要：

  The optically active enantiomers of 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl] -2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-41061, 1) were enantioselectively synthesized. The chiral acetate ((R)-(-)-3) and the chiral alcohol ((S)-(+)-2) were prepared via the resolution of the racemic alcohol ((+/-)-2) using the lipase-mediated transesterification with vinyl acetate. Compounds ((R)-(-)-3) and ((S)-(+)-2) were converted to optically active 1.

  DOI：

  10.3987/com-99-s(i)2
• 作为产物：
  描述：

  (S)-7-chloro-5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 在 吡啶 、 sodium hydride 、 magnesium 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 (S)-7-chloro-5-methoxymethyloxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  An Efficient Synthesis of Optical Isomers of Vasopressin V2 Receptor Antagonist OPC-41061 by Lipase-catalyzed Enantioselective Transesterification

  摘要：

  The optically active enantiomers of 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl] -2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-41061, 1) were enantioselectively synthesized. The chiral acetate ((R)-(-)-3) and the chiral alcohol ((S)-(+)-2) were prepared via the resolution of the racemic alcohol ((+/-)-2) using the lipase-mediated transesterification with vinyl acetate. Compounds ((R)-(-)-3) and ((S)-(+)-2) were converted to optically active 1.

  DOI：

  10.3987/com-99-s(i)2