(R)-7-(3',4,4',5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine | 1260216-17-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (R)-7-(3',4,4',5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine
• 英文别名: 7-(3',4,4',5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine
• CAS: 1260216-17-8
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: VLASJWJSCDHDLG-GOSISDBHSA-N

物化性质

• 沸点：
  528.9±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-7-(3',4,4',5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine 在 三氟代氧化钒(V) 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.33h， 以89%的产率得到(R)-tylophorine
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954
• 作为产物：
  描述：

  (R)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 在 叔丁基锂 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 9.42h， 生成 (R)-7-(3',4,4',5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954