(+/-)-3-(3'-bromo-2'-hydroxy-3'-methylbutyl)-4,8-dimethoxy-2-quinolinone | 159973-41-8

• 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: (+/-)-3-(3'-bromo-2'-hydroxy-3'-methylbutyl)-4,8-dimethoxy-2-quinolinone
• 英文别名: 3-(3-bromo-2-hydroxy-3-methylbutyl)-4,8-dimethoxy-1H-quinolin-2-one
• CAS: 159973-41-8
• 化学式: C₁₆H₂₀BrNO₄
• 分子量: 370.243
• InChiKey: BNMOHNAOQWNRRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(3'-bromo-2'-hydroxy-3'-methylbutyl)-4,8-dimethoxy-2-quinolinone 在 4-二甲氨基吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 96.0h， 生成 (S)-2,3-dihydro-2-(1'-hydroxyisopropyl)-4,8-dimethoxyfurano<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
• 作为产物：
  描述：

  (+/-)-2-benzyloxy-3-(2',3'-epoxy-3'-methylbutyl)-4,8-dimethoxyquinoline 在 氢溴酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以55%的产率得到(+/-)-3-(3'-bromo-2'-hydroxy-3'-methylbutyl)-4,8-dimethoxy-2-quinolinone
  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.