(-)-(2'S,2''R)-3-<3'-bromo-2'-(2''-methoxy-2''-phenyl-2''-trifluoromethylacetoxy)-3'-methylbutyl>-2,4,8-trimethoxyquinoline | 159973-36-1

• 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: (-)-(2'S,2''R)-3-<3'-bromo-2'-(2''-methoxy-2''-phenyl-2''-trifluoromethylacetoxy)-3'-methylbutyl>-2,4,8-trimethoxyquinoline
• 英文别名: [(2S)-3-bromo-3-methyl-1-(2,4,8-trimethoxyquinolin-3-yl)butan-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 159973-36-1
• 化学式: C₂₇H₂₉BrF₃NO₆
• 分子量: 600.43
• InChiKey: UXCMPFAXEQRIAQ-RXFWQSSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (-)-(2'S,2''R)-3-<3'-bromo-2'-(2''-methoxy-2''-phenyl-2''-trifluoromethylacetoxy)-3'-methylbutyl>-2,4,8-trimethoxyquinoline 在 锂硼氢 、 硼烷 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (-)-(2'S)-3-(2'-hydroxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline
  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：

  (+/-)-3-(2',3'-epoxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 在 4-二甲氨基吡啶 、 氢溴酸 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 72.5h， 生成 (-)-(2'S,2''R)-3-<3'-bromo-2'-(2''-methoxy-2''-phenyl-2''-trifluoromethylacetoxy)-3'-methylbutyl>-2,4,8-trimethoxyquinoline
  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.