desmethoxytylophorine | 1260216-24-7

• 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: desmethoxytylophorine
• 英文别名: 2,3,7-Trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
• CAS: 1260216-24-7
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: VETDZFCQDQOPFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

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) 、 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 desmethoxytylophorine
  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

• Cyano Group Removal from Cyano-Promoted Aza-Diels–Alder Adducts: Synthesis and Structure–Activity Relationship of Phenanthroindolizidines and Phenanthroquinolizidines
  作者：Chi-Fen Chang、Chien-Fu Li、Chia-Chen Tsai、Ta-Hsien Chuang

  DOI：10.1021/acs.orglett.5b03395

  日期：2016.2.19

  Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels–Alder cycloadducts followed by aryl–aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments

  通过氰基促进的分子内氮杂-Diels-Alder环加合物的还原脱氰作用，然后进行芳基-芳基偶联，可以精确合成苯并菲吲哚并菲和菲并喹啉并菲。通过在2-丙醇中用硼氢化钠处理以几乎定量的产率从α-氨基丙烯腈中除去氰基。提出了一种可能的机制，并使用D标记实验进行了研究。讨论了菲取代模式对三种人类癌细胞系抗癌活性影响的系统研究。
• PHENANTHROINDOLIZIDINE ANALOGUES
  申请人：Lee Shiow-Ju

  公开号：US20100216773A1

  公开（公告）日：2010-08-26

  Treatment of coronavirus infection with phenanthroindolizidine analogues.

  使用菲南三氮杂环吲哚啉类似物治疗冠状病毒感染。
• One-Pot Oxidative Coupling/Decyanation of 6,7-Diphenylindolizine-5-carbonitriles and 2,3-Diphenylquinolizine-4-carbonitriles
  作者：Yi-Hsuan Chen、Rong-Shiow Tang、Li-Yuan Chen、Ta-Hsien Chuang

  DOI：10.1021/acs.joc.9b00041

  日期：2019.4.5

  The one-pot oxidative coupling/decyanation reactions of 6,7-diphenylindolizine-5-carbonitriles and 2,3-diphenylquinolizine-4-carbonitriles were investigated using aryl–aryl oxidative coupling reagents. The phenanthroindolizidinones and phenanthroquinolizidinones were produced in 52–89% yields under VOF3/trifluoroacetic acid or [bis(trifluoroacetoxy)iodo]benzene/BF3-mediated conditions. This represents

  使用芳基-芳基氧化偶联剂研究了6,7-二苯基吲哚嗪-5腈和2,3-二苯基喹唑嗪-4-腈的一锅氧化偶联/脱氰反应。在VOF 3 /三氟乙酸或[双（三氟乙酰氧基）碘]苯/ BF 3介导的条件下，菲咯啉吲哚酮和菲喹啉酮的产率为52–89％。这代表了从相应的氰基活化的aza-Diels-Alder环加成物构建这些类型的五环骨架的温和而有效的方法。提出了单锅氧化偶联/脱氰反应的合理机理。
• US8440649B2
  申请人：——

  公开号：US8440649B2

  公开（公告）日：2013-05-14
• 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.