tert-butyl (1S)-1-(acetyloxymethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate | 1426429-42-6

• 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: tert-butyl (1S)-1-(acetyloxymethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1426429-42-6
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: LPIIZSUCRVSLAQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S)-1-(acetyloxymethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 盐酸 、 水 、 sodium hydroxide 作用下， 反应 5.0h， 以76%的产率得到萼卷豆碱
  参考文献：
  名称：

  Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: synthesis of calycotomine enantiomers

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.01.006
• 作为产物：
  描述：

  乙酸乙烯酯 、 (±)-tert-butyl 1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 Candida antarctica lipase B 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以43%的产率得到tert-butyl (R)-1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: synthesis of calycotomine enantiomers

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.01.006