(+)-(3S,5S,10bR)-8,9-dimethoxy-5-(3,4-dimethoxyphenyl)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo<2,3-a>isoquinoline | 220850-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+)-(3S,5S,10bR)-8,9-dimethoxy-5-(3,4-dimethoxyphenyl)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo<2,3-a>isoquinoline
• 英文别名: (3S,5S,10bR)-5-(3,4-dimethoxyphenyl)-8,9-dimethoxy-3-phenyl-3,5,6,10b-tetrahydro-2H-[1,3]oxazolo[2,3-a]isoquinoline
• CAS: 220850-44-2
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: WAAXIUCMSFNZCQ-OREGWCPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(3S,5S,10bR)-8,9-dimethoxy-5-(3,4-dimethoxyphenyl)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo<2,3-a>isoquinoline 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 生成 (-)-(1R,3S)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline
  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 、 碘 、 sodium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (+)-(3S,5S,10bR)-8,9-dimethoxy-5-(3,4-dimethoxyphenyl)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo<2,3-a>isoquinoline
  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