2,3-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline | 30061-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
• 英文别名: 2,3-Dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
• CAS: 30061-38-2
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: MDMIGAZBGNORSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴-2-碘-4,5-二甲氧基苯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三氟代氧化钒(V) 、 4',5'-dimethoxy-1,1':2',1''-terphenyl 、 叔丁基锂 、 sodium carbonate 、 三氟乙酸 、 三氟乙酸酐 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 20.5h， 生成 2,3-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
  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 and structure–activity studies of antofine analogues as potential anticancer agents
  作者：Ye Fu、Sang Kook Lee、Hye-Young Min、Taeho Lee、Jaekwang Lee、Maosheng Cheng、Sanghee Kim

  DOI：10.1016/j.bmcl.2006.09.080

  日期：2007.1

  Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.