(R)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate | 1260216-08-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate
• 英文别名: [(8aR)-1,2,3,5,8,8a-hexahydroindolizin-7-yl] trifluoromethanesulfonate
• CAS: 1260216-08-7
• 化学式: C₉H₁₂F₃NO₃S
• 分子量: 271.26
• InChiKey: JCZAUIUTXAWVIG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate 、 2-bromo-3',4,4',5-tetramethoxy-1,1'-biphenyl 在 叔丁基锂 、 zinc dibromide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以98%的产率得到(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
• 作为产物：
  描述：

  (R)-tert-butyl 2-(2-oxobut-3-yn-1-yl)pyrrolidine-1-carboxylate 在 甲醇 、 甲酸 、 L-Selectride 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 (R)-1,2,3,5,8,8a-hexahydroindolizin-7-yl trifluoromethanesulfonate
  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

文献信息

• Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling
  作者：Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/ol1023954

  日期：2011.1.21

  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.