(E,E)-dibutyl 3,3'-[3-bromo-N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]diacrylate | 1423075-21-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E,E)-dibutyl 3,3'-[3-bromo-N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]diacrylate
• CAS: 1423075-21-1
• 化学式: C₃₁H₃₁BrN₂O₆S
• 分子量: 639.567
• InChiKey: AZTLQYOUBQZUQB-WXUKJITCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  104.56
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 3-bromo-N-(2-pyridyl)sulfonyl carbazole 在 palladium diacetate 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 作用下， 以 1,2-二氯乙烷 为溶剂， 以59%的产率得到(E,E)-dibutyl 3,3'-[3-bromo-N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]diacrylate
  参考文献：
  名称：

  Pd^II-Catalyzed Di-o-olefination of Carbazoles Directed by the Protecting N-(2-Pyridyl)sulfonyl Group

  摘要：

  Despite the significance of carbazole in pharmacy and material science, examples of the direct C-H functionalization of this privileged unit are quite rare. The N-(2-pyridyl)sulfonyl group enables the Pd-II-catalyzed ortho-olefination of carbazoles and related systems, acting as both a directing and readily removable protecting group. This method features ample structural versatility, affording typically the double ortho-olefination products (at Cl and C8) in satisfactory yields and complete regiocontrol. The application of this procedure to related heterocyclic systems, such as indoline, is also described.

  DOI：

  10.1021/ol400206k