(+)-(3S)-2-(2,2-diethoxyethyl)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline | 220850-50-0

• 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)-2-(2,2-diethoxyethyl)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (3S)-2-(2,2-diethoxyethyl)-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 220850-50-0
• 化学式: C₂₅H₃₅NO₆
• 分子量: 445.556
• InChiKey: SWPZCFCOUTYUNT-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-(3S)-2-(2,2-diethoxyethyl)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 (+/-)-5β-hydroxy-2,3,10,11-tetramethoxytetrahydroprotoberberine 、 (-)-(5S,14S)-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
• 作为产物：
  描述：

  NSC26679 在 盐酸 、 potassium carbonate 作用下， 反应 2.0h， 生成 (+)-(3S)-2-(2,2-diethoxyethyl)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-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

文献信息

• Chiral Amino Alcohols As Intermediates in the Stereocontrolled Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines and Protoberberines
  作者：Luisa Carrillo、Dolores Badía、Esther Domínguez、Eneritz Anakabe、Iñaki Osante、Imanol Tellitu、José L. Vicario

  DOI：10.1021/jo981326h

  日期：1999.2.1

  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.