2-chloro-8-(2-nitrophenyl)-1-azaazulene | 880767-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-8-(2-nitrophenyl)-1-azaazulene
• 英文别名: 2-Chloro-8-(2-nitrophenyl)cyclohepta[b]pyrrole
• CAS: 880767-19-1
• 化学式: C₁₅H₉ClN₂O₂
• 分子量: 284.702
• InChiKey: QGHGENQNFGLEMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-chloro-1-azaazulene 、 2-硝基碘苯 以54%的产率得到2-chloro-8-(2-nitrophenyl)-1-azaazulene
  参考文献：
  名称：

  Effective Methods for Introducing Some Aryl and Heteroaryl Substituent onto 1-Azaazulene Nuclei

  摘要：

  Introduction of aryl and heteroaryl groups onto 1-azaazulene ring was achieved by addition-elimination reaction and Suzuki coupling. Reaction of 2-chloro-1-azaazulenes with 2-aryllithium and 2-heteroaryllithium followed by dehydrogenation with o-chloranil gave 8-aryl- and 8-heteroaryl-2-chloro-1-azaazulene in good yields. Suzuki coupling of 3-iodo-1-azaazulenens with phenylboronic acid in the presence of Pd catalyst afforded 3-phenyl-1-azaazulenes in excellent yield. Suzuki coupling of 2-bromo-1-azaazulenes with phenylboronic acid gave 2-phenyl-1-azaazulenes. Suzuki coupling of 2,3-dibromo-1-azaazulene with phenylboronic acid preferentially occurred at C-2. Reaction of 3-iodo-1-azaazulene with bis(pinacolato)diboron produced 3,3'-bis(1-azaazulene) derivative.

  DOI：

  10.3987/com-05-s(k)10