(R)-7-chloro-5-methoxymethyloxy-2,3,4,5-tetrahydro-1H-1-benzazepine | 331947-60-5

• 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: (R)-7-chloro-5-methoxymethyloxy-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: (5R)-7-chloro-5-(methoxymethoxy)-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS: 331947-60-5
• 化学式: C₁₂H₁₆ClNO₂
• 分子量: 241.718
• InChiKey: IKRSWSLDEHSZKF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-7-chloro-5-methoxymethyloxy-2,3,4,5-tetrahydro-1H-1-benzazepine 在 吡啶 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-(+)-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：

  (R)-5-acetoxy-7-chloro-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 在 sodium hydride 、 potassium carbonate 、 magnesium 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (R)-7-chloro-5-methoxymethyloxy-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