6-(3-pyridyl)azulene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 6-(3-pyridyl)azulene
• 英文别名: 3-Azulen-6-ylpyridine；3-azulen-6-ylpyridine
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: BSFKETITMPEEJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吡啶 、 6-(3-pyridyl)azulene 在 三氟乙酸酐 、 potassium hydroxide 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 3.5h， 以82%的产率得到6-(3-pyridyl)-1,3-di(4-pyridyl)azulene
  参考文献：
  名称：

  Synthesis of 2-Aryl- and 6-Heteroaryl-1,3-di(4-pyridyl)azulenes by Katritzky’s Pyridylation of 2-Aryl- and 6-Heteroarylazulenes

  摘要：

  Preparation of 2-aryl- and 6-heteroarylazulenes 2-6 and 8-10 was established by the palladium-catalyzed cross-coupling reaction of the corresponding haloazulenes with lithium aryl- and heteroarylmagnesium ate complexes, which were readily prepared from the corresponding aryl and heteroaryl halides. The reaction of 2-6 and 8-10, except for 3 and 8, with pyridine in the presence of Tf2O, followed by treatment with KOH in MeOH afforded the corresponding 2-aryl- and 6-heteroary1-1,3-di(4-pyridyl)azulenes 11-16 in good yields.

  DOI：

  10.3987/com-14-13102
• 作为产物：
  描述：

  3-溴吡啶 、 6-溴薁 在 正丁基锂 、 正丁基氯化镁 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 25.0h， 以70%的产率得到6-(3-pyridyl)azulene
  参考文献：
  名称：

  Synthesis of 2-Aryl- and 6-Heteroaryl-1,3-di(4-pyridyl)azulenes by Katritzky’s Pyridylation of 2-Aryl- and 6-Heteroarylazulenes

  摘要：

  Preparation of 2-aryl- and 6-heteroarylazulenes 2-6 and 8-10 was established by the palladium-catalyzed cross-coupling reaction of the corresponding haloazulenes with lithium aryl- and heteroarylmagnesium ate complexes, which were readily prepared from the corresponding aryl and heteroaryl halides. The reaction of 2-6 and 8-10, except for 3 and 8, with pyridine in the presence of Tf2O, followed by treatment with KOH in MeOH afforded the corresponding 2-aryl- and 6-heteroary1-1,3-di(4-pyridyl)azulenes 11-16 in good yields.

  DOI：

  10.3987/com-14-13102

文献信息

• The Synthesis of Heteroarylazulene
  作者：Noboru Morita、Taku Shoji、Shigeru Kikuchi、Shunji Ito

  DOI：10.3987/com-05-s(k)35

  日期：——
• Synthesis of 2-Aryl- and 6-Heteroaryl-1,3-di(4-pyridyl)azulenes by Katritzky’s Pyridylation of 2-Aryl- and 6-Heteroarylazulenes
  作者：Taku Shoji、Akifumi Maruyama、Shunji Ito、Tetsuo Okujima、Masafumi Yasunami、Junya Higashi、Noboru Morita

  DOI：10.3987/com-14-13102

  日期：——

  Preparation of 2-aryl- and 6-heteroarylazulenes 2-6 and 8-10 was established by the palladium-catalyzed cross-coupling reaction of the corresponding haloazulenes with lithium aryl- and heteroarylmagnesium ate complexes, which were readily prepared from the corresponding aryl and heteroaryl halides. The reaction of 2-6 and 8-10, except for 3 and 8, with pyridine in the presence of Tf2O, followed by treatment with KOH in MeOH afforded the corresponding 2-aryl- and 6-heteroary1-1,3-di(4-pyridyl)azulenes 11-16 in good yields.