1-[(4-甲基苯基)磺酰]-2,3,4,5-四氢-1H-1-苯并吖庚英-5-醇 | 19673-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(4-甲基苯基)磺酰]-2,3,4,5-四氢-1H-1-苯并吖庚英-5-醇
• 英文名称: 5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: 5-hydroxy-2,3,4,5-tetrahydro-1-(p-toluenesulfonyl)-1H-benzazepine；1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol；5-Hydroxy-1-tosyl-2,3,4,5-tetrahydro-1H-benzoazepin；1-[(4-Methylphenyl)sulfonyl]-2,3,4,5-tetrahydro-1h-1-benzazepin-5-ol；1-(4-methylphenyl)sulfonyl-2,3,4,5-tetrahydro-1-benzazepin-5-ol
• CAS: 19673-33-7
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: UUQNDKFZKZJVTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(4-甲基苯基)磺酰]-2,3,4,5-四氢-1H-1-苯并吖庚英-5-醇 在 Lipase QL 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 27.5h， 生成 (R)-5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Enantioselective Synthesis of the Metabolites of Vasopressin V2 Receptor Antagonist OPC-31260 via Lipase-Catalyzed Transesterification

  摘要：

  The optical isomers of 5-dimethylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-31260, 1) and its metabolites (2, 3, 4, 5 and 6) were enantioselectively synthesized. The chiral acetate 8b and alcohol 7a were prepared via the resolution of the racemic alcohol (+/-)-7 using the lipase-mediated transesterification in vinyl acetate. The compounds 8b and 7a were converted to the hydroxy metabolites (2a and 2b), the methylamine metabolites (3a and 3b), the dimethylamines (1a and 1b), and the amine metabolites (4a and 4b) in several steps while maintaining their absolute configurations. The 4,5-diol metabolites (5a, 5b, 6a and 6b) were synthesized from the key intermediates obtained by the lipase-catalyzed transesterification. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00388-4
• 作为产物：
  描述：

  1-(甲苯-4-磺酰基)-1,2,3,4-四氢苯并[b]氮杂卓-5-酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-[(4-甲基苯基)磺酰]-2,3,4,5-四氢-1H-1-苯并吖庚英-5-醇
  参考文献：
  名称：

  Matsubara, Jun; Otsubo, Kenji; Kawano, Yoshikazu, Heterocycles, 2000, vol. 52, # 1, p. 81 - 84

  摘要：

  DOI：