(S)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester
• 英文别名: ethyl (1S)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: UGKCIAQBKIVOHH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[2-(3-methoxyphenyl)-ethyl]oxalamic acid ethyl ester 在 Candida antarctica lipase B 、 ammonium hydroxide 、 platinum on activated charcoal 、 ammonium acetate 、 水 、 氢气 、 三氯氧磷 作用下， 反应 48.0h， 生成 (R)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 、 (S)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Efficient dynamic kinetic resolution method for the synthesis of enantiopure 6-hydroxy- and 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

  摘要：

  Enantiomeric 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), useful in the synthesis of modulators of nuclear receptors, including liver X receptor and its analogue 6-methoxy-1,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (ee >99%), a source of the above enantiomer was synthesized through Candida antarctica lipase B-catalysed dynamic kinetic hydrolysis of the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters (+/-)-4 center dot HCl and (+/-)-5. (R)-Selective hydrolysis in both organic solvents and an aqueous NH4OAc buffer at pH 8.5 was observed and the amino acids were obtained in good chemical yields (>87%). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.011

文献信息

• Efficient dynamic kinetic resolution method for the synthesis of enantiopure 6-hydroxy- and 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
  作者：Enikő Forró、Rita Megyesi、Tihamér A. Paál、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2016.10.011

  日期：2016.12

  Enantiomeric 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), useful in the synthesis of modulators of nuclear receptors, including liver X receptor and its analogue 6-methoxy-1,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (ee >99%), a source of the above enantiomer was synthesized through Candida antarctica lipase B-catalysed dynamic kinetic hydrolysis of the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters (+/-)-4 center dot HCl and (+/-)-5. (R)-Selective hydrolysis in both organic solvents and an aqueous NH4OAc buffer at pH 8.5 was observed and the amino acids were obtained in good chemical yields (>87%). (C) 2016 Elsevier Ltd. All rights reserved.