tert-butyl (1S)-1-(2-hydroxyethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate | 1426429-43-7

• 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: tert-butyl (1S)-1-(2-hydroxyethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1426429-43-7
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: ZHUXXTUZCJUMMW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S)-1-(2-hydroxyethyl)-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-[(1S)-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
• 作为产物：
  描述：

  乙酸乙烯酯 、 在 sodium sulfate 、 三乙胺 作用下， 以 甲苯 为溶剂， 以97%的产率得到
  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

• Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: synthesis of calycotomine enantiomers
  作者：László Schönstein、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2013.01.006

  日期：2013.2

  Both enantiomers of calycotomine (R)-5 and (S)-5 were prepared through the CAL-B-catalysed asymmetric O-acylation of N-Boc-protected (6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol [(+/-)-3)]. The optimum conditions for the enzymatic resolution were determined under continuous-flow conditions, while the preparative-scale resolution of (+/-)-3 was performed as a batch reaction with high enantiselectivity (E>200). The resulting amino alcohol (S)-3 and amino ester (R)-4, obtained with high enantiomeric excess (ee = 99%), were transformed into the desired calycotomine (S)-5 and (R)-5 (ee = 99%). A systematic study was carried out in a continuous-flow system on the O-acylation of tetrahydroisoquinoline amino alcohol homologues (+/-)-1 to (+/-)-3 containing a remote stereogenic centre. (C) 2013 Elsevier Ltd. All rights reserved.