(+/-)-2-methoxyethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate | 1139908-69-2

• 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: (+/-)-2-methoxyethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate
• CAS: 1139908-69-2
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: QZJBUMXGMAHORK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2-methoxyethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate 在 lipase PS-D 、 水 作用下， 以 异丙醚 为溶剂， 反应 18.0h， 生成 (S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetic acid 、 (R)-2-methoxyethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters

  摘要：

  The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E>200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.032
• 作为产物：
  描述：

  乙二醇甲醚 、 1-乙氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 硫酸 作用下， 以32%的产率得到(+/-)-2-methoxyethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters

  摘要：

  The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E>200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.032