2,3-dibromo-1-azaazulene | 872287-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,3-dibromo-1-azaazulene
• 英文别名: 2,3-Dibromocyclohepta[b]pyrrole
• CAS: 872287-33-7
• 化学式: C₉H₅Br₂N
• 分子量: 286.953
• InChiKey: PIYNCBFJLKFRQK-UHFFFAOYSA-N

物化性质

• 沸点：
  322.5±42.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  2,3-dibromo-1-azaazulene 、 反式-BETA-苯乙烯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以88%的产率得到3-bromo-2-[(E)-2-phenylethenyl]cyclohepta[b]pyrrole
  参考文献：
  名称：

  Syntheses of 2-Formyl-, 2,3-Diformyl- and 8-Formyl-1-azaazulenes

  摘要：

  DOI：

  10.3987/com-07-s(u)6
• 作为产物：
  描述：

  2-bromo-1-azaazulene 在 溴 、 溶剂黄146 作用下， 生成 2,3-dibromo-1-azaazulene
  参考文献：
  名称：

  Nozoe et al., Chemistry and industry, 1954, p. 1357

  摘要：

  DOI：

文献信息

• Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene
  作者：Keito Ohtsu、Ryohei Hayami、Takuya Sagawa、Satoru Tsukada、Kazuki Yamamoto、Takahiro Gunji

  DOI：10.1016/j.tet.2019.130658

  日期：2019.11

  Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, ultraviolet–visible (UV–Vis) spectroscopy, cyclic voltammetry

  使用Sonogashira-Hagihara交叉偶联反应，然后用浓磷酸脱羧，合成了两种化合物6-（1-（氮杂氮烯-2-基）乙炔基氮杂烯（8）和6-（2-氮杂烯基）乙炔基氮杂烯（10）。化合物8和10的特征在于1 H和13 C核磁共振（NMR）光谱，质谱，紫外可见（UV-Vis）光谱，循环伏安法和密度泛函理论（DFT）计算。根据该结果，证实两种化合物在其整个分子结构中均具有π共轭。化合物8和10的酸响应度使用UV-Vis和1 H NMR光谱进行了评估。发现化合物8对三氟乙酸高度敏感，其1-氮杂氮烯基部分充当碱。当与过量的三氟乙酸混合时，化合物10产生z阳离子。
• Synthesis of 2-Arylamino-1-azaazulenes
  作者：Satoru Tsukada、Makoto Nakazawa、Yuya Okada、Keito Ohtsu、Noritaka Abe、Takahiro Gunji

  DOI：10.3987/com-16-s(s)48

  日期：——

  A series of 2-arylamino-l-azaazulenes were synthesized by the Buchwald-Hartwig cross coupling reaction. The resulting compounds were characterized by H-1 NMR, C-13 NMR, HRMS analyses, and elemental analysis. X-Ray crystallographic analysis revealed that 2-(1-naphthylamino)-1-azaazuleneexists in dimeric form with two intermolecular N-H center dot center dot center dot N hydrogen bonds in its crystal structure.
• Effective Methods for Introducing Some Aryl and Heteroaryl Substituent onto 1-Azaazulene Nuclei
  作者：Noritaka Abe、Megumi Tanaka、Takeshi Maeda、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-05-s(k)10

  日期：——

  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.
• Synthesis of Aryl Conjugated (1-Azaazulenyl)acetylenes and Facile Synthesis of Thiophene Fused 1-Azaazulenes
  作者：Noritaka Abe、Yohei Harada、Yukiko Imachi、Hiroyuki Fujii、Akikazu Kakehi、Motoo Shiro

  DOI：10.3987/com-06-s(k)37

  日期：——

  3-Ethynyl-1-azaazulene derivatives were obtained by Sonogashira-Hagihara reaction of 3-iodo-2-chloro-1-azaazulenes, and 2-(phenylethynyl)-1-azaazulenes were obtained by the reaction of 2-bromo-1-azaazulenes. Glaser reaction of 2-chloro-3-ethynyl-1-azaazulenes gave 1,4-bis(2-chloro-1-azaazulen-3-yl)-1,3-butadiyne. Treatment of 2-chloro-3-ethynyl-1-azaazulene derivatives with sodium hydrosulfide gave corresponding 1-thia-9-azacyclopent[a]azulene derivatives in good yield.