(E,E)-1,1'-[N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]bis(pent-1-en-3-one) | 1423075-10-8

• 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)-1,1'-[N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]bis(pent-1-en-3-one)
• CAS: 1423075-10-8
• 化学式: C₂₇H₂₄N₂O₄S
• 分子量: 472.565
• InChiKey: GDPZCMZNQYTNNN-YXLFCKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.1
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  吡啶-2-磺酰氯 在 palladium diacetate 、 sodium hydride 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (E,E)-1,1'-[N-(2-pyridyl)sulfonyl-9H-carbazole-1,8-diyl]bis(pent-1-en-3-one)
  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