(+)-(3S,2'R)-3-(2'-methoxy-2'-phenyl-2'-trifluoromethylacetoxy)-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-2H-pyrano<2,3-b>quinoline | 159973-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+)-(3S,2'R)-3-(2'-methoxy-2'-phenyl-2'-trifluoromethylacetoxy)-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-2H-pyrano<2,3-b>quinoline
• 英文别名: [(3S)-5,9-dimethoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]quinolin-3-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 159973-44-1
• 化学式: C₂₆H₂₆F₃NO₆
• 分子量: 505.491
• InChiKey: ZTJMOQSJCCXVFA-UQBPGWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (+)-(3S,2'R)-3-(2'-methoxy-2'-phenyl-2'-trifluoromethylacetoxy)-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-2H-pyrano<2,3-b>quinoline 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到9-methoxygeibalansine
  参考文献：
  名称：

  Resolution of prenyl bromohydrin esters and derivatives: synthesis of the quinoline alkaloid (+)-(R)- and (−)-(S)- lunacridine

  摘要：

  Chromatographic separation of the bromohydrin MTPA diastereoisomers formed at the prenyl group attached to quinoline and coumarin rings is reported; base catalysed cyclization of the bromo MTPA esters in the quinoline series yielded the corresponding prenyl epoxide enantiomers. This provides a synthetic route to the enantiopure quinoline alkaloid lunacridine 11 and to the dihydrofuroquinoline 8-methoxy-platydesmine 8.

  DOI：

  10.1016/s0040-4020(01)89424-2
• 作为产物：
  描述：

  4,8-dimethoxy-3-(3'-methylbut-2'-enyl)-2-quinolinone 在 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 氢溴酸 、 potassium carbonate 、 间氯过氧苯甲酸 、 potassium iodide 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 120.5h， 生成 (+)-(3S,2'R)-3-(2'-methoxy-2'-phenyl-2'-trifluoromethylacetoxy)-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-2H-pyrano<2,3-b>quinoline
  参考文献：
  名称：

  Resolution of prenyl bromohydrin esters and derivatives: synthesis of the quinoline alkaloid (+)-(R)- and (−)-(S)- lunacridine

  摘要：

  Chromatographic separation of the bromohydrin MTPA diastereoisomers formed at the prenyl group attached to quinoline and coumarin rings is reported; base catalysed cyclization of the bromo MTPA esters in the quinoline series yielded the corresponding prenyl epoxide enantiomers. This provides a synthetic route to the enantiopure quinoline alkaloid lunacridine 11 and to the dihydrofuroquinoline 8-methoxy-platydesmine 8.

  DOI：

  10.1016/s0040-4020(01)89424-2

文献信息

• Resolution of prenyl bromohydrin esters and derivatives: synthesis of the quinoline alkaloid (+)-(R)- and (−)-(S)- lunacridine
  作者：Stephen A. Barr、Derek R. Boyd、Narain D. Sharma、Timothy A. Evans、John F. Malone、Vimal D. Mehta

  DOI：10.1016/s0040-4020(01)89424-2

  日期：1994.1

  Chromatographic separation of the bromohydrin MTPA diastereoisomers formed at the prenyl group attached to quinoline and coumarin rings is reported; base catalysed cyclization of the bromo MTPA esters in the quinoline series yielded the corresponding prenyl epoxide enantiomers. This provides a synthetic route to the enantiopure quinoline alkaloid lunacridine 11 and to the dihydrofuroquinoline 8-methoxy-platydesmine 8.