(-)-(5S,6S,14S)-6-phenyl-2,3,10,11-tetramethoxy-7,8,13,14-tetrahydroprotoberberin-5-ol | 220850-48-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: (-)-(5S,6S,14S)-6-phenyl-2,3,10,11-tetramethoxy-7,8,13,14-tetrahydroprotoberberin-5-ol
• 英文别名: (5S,6S,13aS)-2,3,10,11-tetramethoxy-6-phenyl-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinolin-5-ol
• CAS: 220850-48-6
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: WFUOTNGFCWTSLG-PUUVEUEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (-)-(5S,6S,14S)-6-phenyl-2,3,10,11-tetramethoxy-7,8,13,14-tetrahydroprotoberberin-5-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以60%的产率得到(-)-(5S,6S,14S)-5-acetoxy-6-phenyl-2,3,10,11-tetramethoxy-7,8,13,14-tetrahydroprotoberberine
  参考文献：
  名称：

  Chiral Amino Alcohols As Intermediates in the Stereocontrolled Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines and Protoberberines

  摘要：

  An efficient stereocontrolled synthetic approach to (3S)-3-aryltetrahydroisoquinoline Sd and (1S,3S)-3-aryl-1-methyltetrahydroisoquinolines 3a-c by a Pictet-Spengler heterocyclization reaction of optically active (95% ee) (S)-1,2-diarylethylamines 2a-c is presented. An alternative route toward obtaining the epimeric derivative of 3a, tetrahydroisoquinoline (1R,3S)-6, was also achieved by a stereocontrolled ring opening process carried out on the oxazolotetrahydroisoquinoline 9. Tetrahydroisoquinoline 8 was employed for the stereoselective preparation of(5S,6S, 14S)-6-phenyl-2,3,10,11-tetramethoxyprotoberberin-5-ol (12), a new type of 5,6-disubstituted protoberberine derivative with excellent (d.e>95% by H-1 NMR) stereoselection.

  DOI：

  10.1021/jo981326h
• 作为产物：
  描述：

  (2S)-2-[[(1S)-1,2-bis(3,4-dimethoxyphenyl)ethyl]amino]-2-phenylethanol 在 盐酸 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 7.75h， 生成 (-)-(5S,6S,14S)-6-phenyl-2,3,10,11-tetramethoxy-7,8,13,14-tetrahydroprotoberberin-5-ol
  参考文献：
  名称：

  Chiral Amino Alcohols As Intermediates in the Stereocontrolled Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines and Protoberberines

  摘要：

  An efficient stereocontrolled synthetic approach to (3S)-3-aryltetrahydroisoquinoline Sd and (1S,3S)-3-aryl-1-methyltetrahydroisoquinolines 3a-c by a Pictet-Spengler heterocyclization reaction of optically active (95% ee) (S)-1,2-diarylethylamines 2a-c is presented. An alternative route toward obtaining the epimeric derivative of 3a, tetrahydroisoquinoline (1R,3S)-6, was also achieved by a stereocontrolled ring opening process carried out on the oxazolotetrahydroisoquinoline 9. Tetrahydroisoquinoline 8 was employed for the stereoselective preparation of(5S,6S, 14S)-6-phenyl-2,3,10,11-tetramethoxyprotoberberin-5-ol (12), a new type of 5,6-disubstituted protoberberine derivative with excellent (d.e>95% by H-1 NMR) stereoselection.

  DOI：

  10.1021/jo981326h