(S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinolin-2-ol | 910632-65-4

• 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)-3,4-dihydro-1H-isoquinolin-2-ol
• 英文别名: (1S)-2-hydroxy-1-[(E)-2-phenylethenyl]-3,4-dihydro-1H-isoquinoline
• CAS: 910632-65-4
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: QTAQWWJVNJTIGV-DVQDXYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,4-dihydro-isoquinoline 2-oxide 、 苯乙炔 在 dimethyl sulfide borane 、 cyclohexene adduct at 1:2 molar ratio 、 diethylzinc 、 tert-butyl (S)-(1-cyclohexyl-2-morpholinoethyl)carbamate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinolin-2-ol 、 (R)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinolin-2-ol
  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