(-)-(1S,3S)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline

• 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: (-)-(1S,3S)-6,7-dimethoxy-3-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1S,3S)-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: ATZZRVZVOUWNAV-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  NSC26679 在 palladium on activated charcoal 4-二甲氨基吡啶 、 五氯化磷 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (-)-(1S,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

文献信息

• Determination of the stereochemistry of 1-substituted 3-aryltetrahydroisoquinolines by1H NMR spectroscopy
  作者：Esther Dominguez、Esther Lete、M. Dolores Badia、M. Jesus Villa、Luis Castedo、Domingo Dominguez

  DOI：10.1016/s0040-4020(01)81507-6

  日期：1987.1

  aromatic aldehydes under acidic conditions. However, the epimeric trans-1,3-disubstituted tetrahydroisoquinolines 3 are also isolated as minor products. The stereochemistry of the tetrahydroisoquinolines was unambiguously assigned on the basis of the1H NMR data, and are supported by difference NOE measurements.

  所述顺式-1,3-二取代的四氢异喹啉2可以通过1,2-双（3,4-二甲氧基苯基）在酸性条件下的脂族和芳族醛-乙胺的Pictet Spengler环化生成一个高度非对映的方式来获得。然而，差向异构体反式-1，3-二取代的四氢异喹啉3也作为次要产物被分离出来。基于1 H NMR数据明确分配了四氢异喹啉的立体化学，并由不同的NOE测量值支持。