(+/-)-O-Acetylthaliporphin | 35587-63-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (+/-)-O-Acetylthaliporphin
• 英文别名: (2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-yl) acetate
• CAS: 35587-63-4
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: LFRYFMRULINIJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-O-Acetylthaliporphin 在 水 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 216.0h， 生成 thaliporphine 、 (-)-Thaliporphine
  参考文献：
  名称：

  Lipase-catalyzed Resolution of Acetates of Racemic Phenolic Aporphines and Homoaporphines in Organic Solvent

  摘要：

  Enzymatic resolution of (+/-)-1-acetoxy-2,9,10-trimethoxyaporphine (O-acetylthaliporphine)(3), (+/-)-2-acetoxy-1,9,10-trimethoxyaporphine (O-acetylpredicentrine)(4), and (+/-)-3-acetoxy-2,9,10-trimethoxyaporphines (5) by use of immobilized lipase in organic solvent gave resolved 3-5 and the corresponding hydroxyaporphines (9-11) in fair to good chemical and optical yields. Analogous reaction of (+/-)-1-acetoxy-2,10,11-trimethoxyhomoaporphine (6) did not take place, whereas that of (+/-)-2-acetoxy-1,10,11-trimethoxy- and (+/-)-3-acetoxy-2,10,11-trimethoxyhomoaporphines (7 and 8) produced optical active 7, 8 and hydroxyhomoaporphines (13, 14).

  DOI：

  10.3987/com-94-s(b)40

文献信息

• Lipase-catalyzed Resolution of Acetates of Racemic Phenolic Aporphines and Homoaporphines in Organic Solvent
  作者：Osamu Hoshino、Hiroyuki Fuchino、Masafumi Kikuchi

  DOI：10.3987/com-94-s(b)40

  日期：——

  Enzymatic resolution of (+/-)-1-acetoxy-2,9,10-trimethoxyaporphine (O-acetylthaliporphine)(3), (+/-)-2-acetoxy-1,9,10-trimethoxyaporphine (O-acetylpredicentrine)(4), and (+/-)-3-acetoxy-2,9,10-trimethoxyaporphines (5) by use of immobilized lipase in organic solvent gave resolved 3-5 and the corresponding hydroxyaporphines (9-11) in fair to good chemical and optical yields. Analogous reaction of (+/-)-1-acetoxy-2,10,11-trimethoxyhomoaporphine (6) did not take place, whereas that of (+/-)-2-acetoxy-1,10,11-trimethoxy- and (+/-)-3-acetoxy-2,10,11-trimethoxyhomoaporphines (7 and 8) produced optical active 7, 8 and hydroxyhomoaporphines (13, 14).