(S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester | 910632-69-8

• 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-isoquinoline-2-carboxylic acid benzyl ester
• 英文别名: benzyl (1S)-1-[(E)-2-phenylethenyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 910632-69-8
• 化学式: C₂₅H₂₃NO₂
• 分子量: 369.463
• InChiKey: WOPOWXWCCYTWGC-QDEBQFNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-((E)-Styryl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以61%的产率得到(R)-N-苄氧羰基-3,4-二氢-1H-异喹啉羧酸
  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 、 碳酸氢钠 、 溶剂黄146 、 锌 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (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