tetramethyl 6-bromonaphthalene-1,2,3,4-tetracarboxylate | 39651-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tetramethyl 6-bromonaphthalene-1,2,3,4-tetracarboxylate
• 英文别名: 6-Brom-1,2,3,4-tetramethoxycarbonylnaphthalin
• CAS: 39651-74-6
• 化学式: C₁₈H₁₅BrO₈
• 分子量: 439.216
• InChiKey: ZZKSLKXXAXBLKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  钠盐 、 丁炔二酸二甲酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以65%的产率得到tetramethyl 6-bromonaphthalene-1,2,3,4-tetracarboxylate
  参考文献：
  名称：

  铑催化的芳烃次磺酸钠的脱硫和炔烃的氧化环化

  摘要：

  AbstractPolycyclic aromatic compounds are widely used in materials science, so it is highly desirable to develop an efficient and practical approach to them. In this paper, a novel, efficient and practical method for the rhodium(III)‐catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes has been developed, and the corresponding polycyclic aromatic compounds with multiple substituents were prepared in moderate to good yields. The reactions proceeded through sequential rhodium(III)‐catalyzed desulfination, intermolecular addition of aryl‐Rh(III) complexes to dialkyl but‐2‐ynedioates and diarylalkynes, and intramolecular oxidative annulation via CH activation. The present method is the first example of the oxidative annulation of arene derivatives with two different alkynes. Therefore, it should afford a useful strategy for the synthesis of polycyclic aromatic compounds.magnified image

  DOI：

  10.1002/adsc.201400930