6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile

• 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: 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
• 英文别名: 1,2,3,4-Tetrahydro-6-methoxy-1-isoquinolinecarbonitrile
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: GMQQCGLOUKRCIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 R-1-(3,5-二苄氧基-4-甲氧基苄基)-6-甲氧基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Dihydrocodeine and Formal Synthesis of (−)-Thebaine, (−)-Codeine, and (−)-Morphine from a Deprotonated α-Aminonitrile

  摘要：

  The alpha-benzylation of a deprotonated bicyclic a-aminonitrile, followed by Noyori's asymmetric transfer hydrogenation combined with the Grewe cyclization onto a symmetrical A-ring precursor, are the key steps of a short and high-yielding enantioselective synthesis of the morphinan (-)-dihydrocodeine. This compound can be converted to (-)-thebaine in high yield by known transformations, while (-)-codeine and (-)-morphine are available from an advanced intermediate.

  DOI：

  10.1021/ol5023849
• 作为产物：
  描述：

  6-甲氧基-3,4-二氢-异喹啉 、 丙酮氰醇 以 水 为溶剂， 以92%的产率得到6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Dihydrocodeine and Formal Synthesis of (−)-Thebaine, (−)-Codeine, and (−)-Morphine from a Deprotonated α-Aminonitrile

  摘要：

  The alpha-benzylation of a deprotonated bicyclic a-aminonitrile, followed by Noyori's asymmetric transfer hydrogenation combined with the Grewe cyclization onto a symmetrical A-ring precursor, are the key steps of a short and high-yielding enantioselective synthesis of the morphinan (-)-dihydrocodeine. This compound can be converted to (-)-thebaine in high yield by known transformations, while (-)-codeine and (-)-morphine are available from an advanced intermediate.

  DOI：

  10.1021/ol5023849

文献信息

• Enantioselective Synthesis of (−)-Dihydrocodeine and Formal Synthesis of (−)-Thebaine, (−)-Codeine, and (−)-Morphine from a Deprotonated α-Aminonitrile
  作者：Mario Geffe、Till Opatz

  DOI：10.1021/ol5023849

  日期：2014.10.17

  The alpha-benzylation of a deprotonated bicyclic a-aminonitrile, followed by Noyori's asymmetric transfer hydrogenation combined with the Grewe cyclization onto a symmetrical A-ring precursor, are the key steps of a short and high-yielding enantioselective synthesis of the morphinan (-)-dihydrocodeine. This compound can be converted to (-)-thebaine in high yield by known transformations, while (-)-codeine and (-)-morphine are available from an advanced intermediate.