4H-4a,5-bis(trifluoromethyl)-6-phenyl-7-carbethoxyindolo<2,7,1-cde>quinolizine | 139243-72-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4H-4a,5-bis(trifluoromethyl)-6-phenyl-7-carbethoxyindolo<2,7,1-cde>quinolizine
• 英文别名: ethyl 10-phenyl-11,12-bis(trifluoromethyl)-13-azatetracyclo[10.2.1.05,14.08,13]pentadeca-1(14),2,4,6,8,10-hexaene-9-carboxylate
• CAS: 139243-72-4
• 化学式: C₂₅H₁₇F₆NO₂
• 分子量: 477.406
• InChiKey: AJIIEZVIQANYHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯丙炔酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 以 氯苯 为溶剂， 反应 2.0h， 生成 4H-4a,5-bis(trifluoromethyl)-6-phenyl-7-carbethoxyindolo<2,7,1-cde>quinolizine 、 4H-4a,5-bis(trifluoromethyl)-6-carbethoxy-7-phenylindolo<2,7,1-cde>quinolizine
  参考文献：
  名称：

  Reactivity of cyclopalladated compounds. 28. Alkyne reactions with the cyclopalladated 8-methylquinoline ligand. Synthesis of novel heterocyclic compounds with a bridgehead nitrogen

  摘要：

  The stepwise reaction of cyclopalladated 8-methylquinoline (compound 1, obtained via intramolecular metalation of 8-methylquinoline by Pd(II)) with 2 equiv of various internal alkynes affords 4H-indolo[2,1,7-cde]quinolizines 3 through simultaneous Pd-mediated C-C and C-N bond formation. This reaction displays a high selectivity provided that the first alkyne reacting with 1 bears two electron-withdrawing substituents such as -CF3 or -CO2Me and that the second alkyne is also substituted by electrophilic substituents. Varying the reaction conditions allowed us to isolate organometallic intermediates, whose nature shed some light upon the mechanism of the formation of 3. Several deviations from the synthesis of 3 were encountered when different alkynes were reacted with 1, e.g., with ethyl-3-phenylpropynoate a four-substituted alpha-pyrone was synthesized through C-O activation of one of the ester functions.

  DOI：

  10.1021/jo00033a042