2-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]ethanol | 1462335-68-7

• 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-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]ethanol
• CAS: 1462335-68-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: VIWOJGACEJJOIU-LLVKDONJSA-N

物化性质

• 熔点：
  106-108 °C
• 沸点：
  399.6±42.0 °C(predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (1R)-1-(2-acetyloxyethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 盐酸 、 sodium hydroxide 作用下， 以71%的产率得到2-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]ethanol
  参考文献：
  名称：

  Enzymatic reactions for the preparation of homocalycotomine enantiomers

  摘要：

  Homocalycotomine enantiomers (R)-4 and (S)-4 were prepared by the Candida antarctica lipase B (CAL-B)-catalysed asymmetric O-acylation of N-Boc-protected 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanol (+/-)-1. The preliminary small-scale experiments were performed either in a continuous-flow system or as batch reactions, while the preparative-scale resolution was carried out in two steps with vinyl acetate as the acyl donor in the presence of Et3N and Na2SO4 in toluene at 3 C, as a batch reaction. Treatment of the resulting amino alcohol (S)-1 and amino ester (R)-3 (ee >= 94%) with 18% HCl, and then with 5 M NaOH, furnished the desired (R)-4 and (S)-4 without a decrease in the enantiomeric excess (ee >= 94%). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.025

文献信息

• Enzymatic reactions for the preparation of homocalycotomine enantiomers
  作者：László Schönstein、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2013.07.025

  日期：2013.9

  Homocalycotomine enantiomers (R)-4 and (S)-4 were prepared by the Candida antarctica lipase B (CAL-B)-catalysed asymmetric O-acylation of N-Boc-protected 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanol (+/-)-1. The preliminary small-scale experiments were performed either in a continuous-flow system or as batch reactions, while the preparative-scale resolution was carried out in two steps with vinyl acetate as the acyl donor in the presence of Et3N and Na2SO4 in toluene at 3 C, as a batch reaction. Treatment of the resulting amino alcohol (S)-1 and amino ester (R)-3 (ee >= 94%) with 18% HCl, and then with 5 M NaOH, furnished the desired (R)-4 and (S)-4 without a decrease in the enantiomeric excess (ee >= 94%). (C) 2013 Elsevier Ltd. All rights reserved.