(R)-ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate | 17447-42-6

• 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: (R)-ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate
• 英文别名: ethyl 2-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]acetate
• CAS: 17447-42-6
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: RLUWHGCQILMZMC-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate 在 水 作用下， 反应 4.0h， 以60%的产率得到(R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetic acid
  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：

  1-乙氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 lipase PS-D 、 水 作用下， 以 异丙醚 为溶剂， 反应 160.0h， 以48%的产率得到(R)-ethyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)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

文献信息

• Kinetic Resolution of Nitrogen Heterocycles with a Reusable Polymer-Supported Reagent
  作者：Imants Kreituss、Yuta Murakami、Michael Binanzer、Jeffrey W. Bode

  DOI：10.1002/anie.201204991

  日期：2012.10.15

  Shake it up baby! Simply shaking a polymer‐supported reagent and the racemic amine at room temperature kinetically resolves a broad range of N‐heterocycles with good selectivity. The polymer‐supported reagents are robust, easy to regenerate, and can be reused dozens of times. Cleavable acyl groups can be used to give access to both amine enantiomers in a single resolution.

  摇摇宝贝！只需在室温下摇晃聚合物支撑的试剂和外消旋胺，就可以动力学分离宽范围的N-杂环，并具有良好的选择性。聚合物支持的试剂坚固耐用，易于再生，可以重复使用数十次。可裂解的酰基可用于以单一分辨率获得两种胺对映体。
• [EN] KINETIC RESOLUTION OF CHIRAL AMINES<br/>[FR] RÉSOLUTION CINÉTIQUE D'AMINES CHIRALES
  申请人：ETH ZUERICH

  公开号：WO2013007371A3

  公开（公告）日：2013-10-03
• Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters
  作者：Tihamér A. Paál、Enikő Forró、Ferenc Fülöp、Arto Liljeblad、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2008.11.032

  日期：2008.12

  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.