(S)-1-((E)-Styryl)-1,2,3,4-tetrahydro-isoquinoline | 910632-72-3

• 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: (S)-1-((E)-Styryl)-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: (1S)-1-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydroisoquinoline
• CAS: 910632-72-3
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: KZZQNUBLEGEKGG-DVQDXYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((E)-Styryl)-1,2,3,4-tetrahydro-isoquinoline 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 以354 mg的产率得到(S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Enantioselective Addition of Vinylzinc Reagents to 3,4-Dihydroisoquinoline N-Oxide

  摘要：

  Ligand 2a promotes the enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield chiral allylic hydroxylamines. With 0.1 equiv of the ligand, the product is obtained in up to 84% ee, whereas with 1.2 equiv of the ligand, the ee is increased to the 90-95% range with a variety of aliphatic, cyclic, and aromatic vinylzinc reagents. This method was used to synthesize the protected unnatural amino acid N-Cbz-D-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid in three steps from the allylic hydroxylamine.

  DOI：

  10.1021/ol0614525
• 作为产物：
  描述：

  (S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinolin-2-ol 在 copper diacetate 、 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-1-((E)-Styryl)-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Enantioselective Addition of Vinylzinc Reagents to 3,4-Dihydroisoquinoline N-Oxide

  摘要：

  Ligand 2a promotes the enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield chiral allylic hydroxylamines. With 0.1 equiv of the ligand, the product is obtained in up to 84% ee, whereas with 1.2 equiv of the ligand, the ee is increased to the 90-95% range with a variety of aliphatic, cyclic, and aromatic vinylzinc reagents. This method was used to synthesize the protected unnatural amino acid N-Cbz-D-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid in three steps from the allylic hydroxylamine.

  DOI：

  10.1021/ol0614525