(R)-6,8-dibromo-5-(2,3-epoxyprop-1-yloxy)-quinoline | 188594-92-5

• 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: (R)-6,8-dibromo-5-(2,3-epoxyprop-1-yloxy)-quinoline
• 英文别名: 6,8-dibromo-5-[[(2R)-oxiran-2-yl]methoxy]quinoline
• CAS: 188594-92-5
• 化学式: C₁₂H₉Br₂NO₂
• 分子量: 359.017
• InChiKey: SAFOEPXFXOQIKN-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-6,8-dibromo-5-(2,3-epoxyprop-1-yloxy)-quinoline 在 10% palladium on active carbon 氢氧化钾 、 超重氢 作用下， 以 甲醇 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 8.0h， 生成 1-[4-(trans-11,11-difluorodibenzo[b,e]bicyclo[5.1.0]oct-5-yl)-piperazin-1-yl]-3-(6,8-ditritioquinolin-5-yl)oxy-(R)-2-propanol
  参考文献：
  名称：

  Synthesis of multidrug resistance modulator LY335979 labeled with deuterium and tritium

  摘要：

  Dideutero and ditritioisotopomers of the multidrug resistance modulator LY335979 were prepared by initial bromination of 5-hydroxyquinoline under acidic conditions followed by Mitsunobu coupling of 6,8-dibromo-5-hydroxyquinoline with (S)-glycidol. Opening of the resulting epoxide with dibenzosuberylpiperazine LY335995 resulted in dibromoanalog of LY335979, which was finally reductively debrominated with deuterium or tritium in the presence of palladium on carbon.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<49::aid-jlcr938>3.0.co;2-m
• 作为产物：
  描述：

  6,8-Dibromo-quinolin-5-ol; hydrobromide 、 (S)-缩水甘油 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(R)-6,8-dibromo-5-(2,3-epoxyprop-1-yloxy)-quinoline
  参考文献：
  名称：

  Synthesis of multidrug resistance modulator LY335979 labeled with deuterium and tritium

  摘要：

  Dideutero and ditritioisotopomers of the multidrug resistance modulator LY335979 were prepared by initial bromination of 5-hydroxyquinoline under acidic conditions followed by Mitsunobu coupling of 6,8-dibromo-5-hydroxyquinoline with (S)-glycidol. Opening of the resulting epoxide with dibenzosuberylpiperazine LY335995 resulted in dibromoanalog of LY335979, which was finally reductively debrominated with deuterium or tritium in the presence of palladium on carbon.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<49::aid-jlcr938>3.0.co;2-m