tert-butyl (1R)-1-(3-decanoyloxypropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate | 1334398-52-5

• 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 (1R)-1-(3-decanoyloxypropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1334398-52-5
• 化学式: C₂₉H₄₇NO₆
• 分子量: 505.695
• InChiKey: MISDDIHICYTTQL-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 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 (1R)-1-(3-decanoyloxypropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 甲醇 、 potassium carbonate 作用下， 反应 8.0h， 以84%的产率得到(R)-tert-butyl 1-(3-hydroxypropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
  参考文献：
  名称：

  Total synthesis of crispine A enantiomers through a Burkholderia cepacia lipase-catalysed kinetic resolution

  摘要：

  Both enantiomers of the antitumour-active alkaloid crispine A (ee = 95%) were synthesised through the Burkholderia cepacia lipase-catalysed acylation of the primary hydroxy group of N-Boc-protected 1-(3-hydroxypropyl)-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline (+/-)-3 and the enantioselective hydrolysis of the corresponding O-decanoate (+/-)-4 [R = (CH2)(8)Me] with a remote, four-atom distant stereogenic centre. High enantioselectivities were observed for the (S)-selective O-acylation with vinyl decanoate in the presence of Et3N and Na2SO4 in t-BuOMe at 45 degrees C (E = 68), and for the (S)-selective hydrolysis with H2O in t-BuOMe at 45 degrees C (E = 52). The enzymatic resolutions, performed in two steps, afforded the key alcohol and ester enantiomers with high enantiomeric excesses (ee >= 94%). Ring-closure reactions of alcohol enantiomers (+)-3 and (-)-3 with thionyl chloride afforded the desired crispine A enantiomers (+)-1 and (-)-1 (ee >= 95%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.026
• 作为产物：
  描述：

  在 Candida antarctica lipase B 、 sucrose 、 Burkholderia cepacia lipase PS 、 水 作用下， 以 甲基叔丁基醚 、 氯仿 为溶剂， 反应 104.0h， 生成 tert-butyl (1R)-1-(3-decanoyloxypropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Total synthesis of crispine A enantiomers through a Burkholderia cepacia lipase-catalysed kinetic resolution

  摘要：

  Both enantiomers of the antitumour-active alkaloid crispine A (ee = 95%) were synthesised through the Burkholderia cepacia lipase-catalysed acylation of the primary hydroxy group of N-Boc-protected 1-(3-hydroxypropyl)-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline (+/-)-3 and the enantioselective hydrolysis of the corresponding O-decanoate (+/-)-4 [R = (CH2)(8)Me] with a remote, four-atom distant stereogenic centre. High enantioselectivities were observed for the (S)-selective O-acylation with vinyl decanoate in the presence of Et3N and Na2SO4 in t-BuOMe at 45 degrees C (E = 68), and for the (S)-selective hydrolysis with H2O in t-BuOMe at 45 degrees C (E = 52). The enzymatic resolutions, performed in two steps, afforded the key alcohol and ester enantiomers with high enantiomeric excesses (ee >= 94%). Ring-closure reactions of alcohol enantiomers (+)-3 and (-)-3 with thionyl chloride afforded the desired crispine A enantiomers (+)-1 and (-)-1 (ee >= 95%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.026

文献信息

• Total synthesis of crispine A enantiomers through a Burkholderia cepacia lipase-catalysed kinetic resolution
  作者：Enikő Forró、László Schönstein、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2011.06.026

  日期：2011.6

  Both enantiomers of the antitumour-active alkaloid crispine A (ee = 95%) were synthesised through the Burkholderia cepacia lipase-catalysed acylation of the primary hydroxy group of N-Boc-protected 1-(3-hydroxypropyl)-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline (+/-)-3 and the enantioselective hydrolysis of the corresponding O-decanoate (+/-)-4 [R = (CH2)(8)Me] with a remote, four-atom distant stereogenic centre. High enantioselectivities were observed for the (S)-selective O-acylation with vinyl decanoate in the presence of Et3N and Na2SO4 in t-BuOMe at 45 degrees C (E = 68), and for the (S)-selective hydrolysis with H2O in t-BuOMe at 45 degrees C (E = 52). The enzymatic resolutions, performed in two steps, afforded the key alcohol and ester enantiomers with high enantiomeric excesses (ee >= 94%). Ring-closure reactions of alcohol enantiomers (+)-3 and (-)-3 with thionyl chloride afforded the desired crispine A enantiomers (+)-1 and (-)-1 (ee >= 95%). (C) 2011 Elsevier Ltd. All rights reserved.