N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine | 1523248-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine
• 英文别名: 5-[2-(benzylamino)ethyl]-2-methoxyphenol
• CAS: 1523248-30-7
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: GEPCVYOIGOWTLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine 、 对溴苯甲醛 在 (R)-3,3′-bis(2,4,6-triisopropylphenyl)-BINOL-phosphoric acid 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 N-benzyl-1-(4-bromophenyl)-7-methoxy-8-hydroxy-1,2,3,4-tetrahydroisoquinoline 、 N-benzyl-1-(4-bromophenyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline 、 N-benzyl-1-(4-bromophenyl)-7-methoxy-8-hydroxy-1,2,3,4-tetrahydroisoquinoline 、 N-benzyl-1-(4-bromophenyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

  摘要：

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.

  DOI：

  10.1021/jo501099h
• 作为产物：
  描述：

  2-(3-(苄氧基)-4-甲氧基苯基)乙胺 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine
  参考文献：
  名称：

  Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

  摘要：

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.

  DOI：

  10.1021/jo501099h

文献信息

• Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines
  作者：Elma Mons、Martin J. Wanner、Steen Ingemann、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1021/jo501099h

  日期：2014.8.15

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.