2-bromo-3,6-dimethoxy-5-(4-bromophenyl)-1,4-benzoquinone | 1110631-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3,6-dimethoxy-5-(4-bromophenyl)-1,4-benzoquinone
• CAS: 1110631-75-8
• 化学式: C₁₄H₁₀Br₂O₄
• 分子量: 402.039
• InChiKey: UWUDCQTUMMZTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,5-dibromo-3,6-dimethoxy-1,4-benzoquinone 、 4-溴苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以66%的产率得到2-bromo-3,6-dimethoxy-5-(4-bromophenyl)-1,4-benzoquinone
  参考文献：
  名称：

  An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-Step Synthesis of Leucomelone

  摘要：

  Two sequential Suzuki coupling reactions have been developed for efficient synthesis of synthetically and biologically important 3,6-disubstituted 2,5-dioxybenzoquinone architectures in a highly chemoselective controlled manner. The method serves as a key step in the total synthesis of leucomelone in three steps and in 61% overall yield.

  DOI：

  10.1021/ol802645f

文献信息

• Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates
  作者：Élodie Pradayrol、Blandine Séon‐Méniel、Samuel Oger、Biraveena Sinniah‐Kandiah、Régis Guillot、Rémi Franco、Martin Souce、Athéna Kasselouri、Alexandre Maciuk、Laurent Evanno

  DOI：10.1002/ejoc.202201152

  日期：2023.2.17

  Six pulvinic acids (pulvinic, pinastric, atromentic, xerocomic, isoxerocomic, variegatic) and a polyporic acid (atromentin) were synthesised. A set of terphenyl-quinones was prepared through sequential Suzuki-Miyaura couplings. Then, a rearrangement into pulvinic bis-lactones was induced by the action of Ac2O/DMSO. Ring openings and deprotections achieved total syntheses. Fluorescence properties of

  合成了六种 pulvinic acids (pulvinic, pinastric, atromentic, xerocomic, isoxerocomic, variegatic) 和多孔酸 (atromentin)。通过连续的 Suzuki-Miyaura 偶联制备了一组三联苯醌。然后，通过 Ac 2 O/DMSO的作用诱导重排为 pulvinic 双内酯。开环和脱保护实现了全合成。确定了双内酯的荧光特性。