2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl | 1260216-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl
• 英文别名: 1-Bromo-2-(2,3-dimethoxyphenyl)-4,5-dimethoxybenzene
• CAS: 1260216-09-8
• 化学式: C₁₆H₁₇BrO₄
• 分子量: 353.213
• InChiKey: XEBQVXRCLXOLAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl 在 三氟代氧化钒(V) 、 叔丁基锂 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.17h， 生成 Tylocrebrin
  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：

  1-溴-2-碘-4,5-二甲氧基苯 、 2,3-二甲氧基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 16.0h， 以72%的产率得到2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl
  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

• Total Synthesis of Phenanthroindolizidines Using Strained Azacyclic Alkynes
  作者：Katie A. Spence、Marie Hoffmann、Neil K. Garg

  DOI：10.1021/acs.orglett.3c01740

  日期：2023.7.14

  We report a concise approach to phenanthroindolizidine alkaloids, wherein strained azacyclic alkynes are intercepted in Pd-catalyzed annulations. Two types of strained intermediates were evaluated: a functionalized piperidyne and a new strained intermediate, an indolizidyne. We show that each can be employed, ultimately allowing access to three natural products: tylophorine, tylocrebine, and isotylocrebine

  我们报告了一种制备菲并吲哚里西啶生物碱的简明方法，其中紧张的氮杂环炔在钯催化的成环中被拦截。评估了两种类型的应变中间体：官能化哌啶和新的应变中间体吲哚嗪。我们证明，每一种都可以使用，最终获得三种天然产物：tylophorine、tylocrebine 和 isotylocrebine。这些努力证明了紧张氮杂环炔化学与过渡金属催化的成功结合，用于构建复杂的杂环。
• 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.