3-bromo-1,5-azulenequinone | 161126-12-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-bromo-1,5-azulenequinone
• 英文别名: 3-Bromoazulene-1,5-dione
• CAS: 161126-12-1
• 化学式: C₁₀H₅BrO₂
• 分子量: 237.052
• InChiKey: LYIZNUKBFOYXPK-UHFFFAOYSA-N

物化性质

• 沸点：
  439.2±44.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-1,5-azulenequinone 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以85%的产率得到3-Chloroazulene-1,5-dione
  参考文献：
  名称：

  Synthesis and Reactivities of 1,5- and 1,7-Azulenequinone Derivatives. A Highly Convenient, One-Pot Synthesis of 3-Bromo-1,5- and −1,7-Azulenequinones by Bromination of Azulene,

  摘要：

  AbstractA very convenient, one‐pot synthesis (over 80% yield) of 3‐bromo‐1,5‐ and −1,7‐azulenequinones has been developed by bromination of azulene in aqueous tetrahydrofuran. Reduction of 3‐bromo‐1,5‐ and −1,7‐azulenequinones with tin or zinc powder in acetic acid gave the parent 1,5‐ and 1,7‐azulenequinones, and further reduction products.

  DOI：

  10.1002/jccs.199800062
• 作为产物：
  描述：

  奥苷菊环 以58%的产率得到
  参考文献：
  名称：

  Nozoe Tetsuo, Wakabayashi Hidetsugu, Shindo Kimio, Kurihara Teruo, Ishika+, Chem. Lett, (1995) N 1, S 25-26

  摘要：

  DOI：

文献信息

• Preparation of Various Azulenequinone Derivatives by a Nucleophilic Substitution of 3-Bromoazulenequinone Synthones
  作者：Tetsuo Nozoe、Hidetsugu Wakabayashi、Kimio Shindo、Sumio Ishikawa

  DOI：10.1246/cl.1995.27

  日期：1995.1

  3-Bromo derivatives of 1,5- and 1,7-azulenequinones easily react with various nucleophiles to give 3-methoxy, phenoxy, p-nitrophenoxy, butylthio, butylamino, p-tolylamino, dimethylamino, 2-hydroxyethylamino, azulenyl, and guaiazulenyl derivatives of the respective azulenequinones almost quantitatively. 3-Bromo-1,5- and -1,7-azulenequinones afford the 2,3-bisbutylthio derivatives under basic conditions

  1,5- 和 1,7- azulenequinones 的 3-Bromo 衍生物很容易与各种亲核试剂反应，得到 3-甲氧基、苯氧基、对硝基苯氧基、丁硫基、丁氨基、对甲苯氨基、二甲氨基、2-羟乙基氨基、薁基和愈创甘油醚基几乎定量的相应芘醌的衍生物。3-Bromo-1,5- 和 -1,7-azulenequinones 在碱性条件下提供 2,3-二丁硫基衍生物。
• A Highly Convenient, One-Pot Synthesis of 3-Bromo-1,5- and -1,7-Azulenequinones by Polybromination of Azulene
  作者：Tetsuo Nozoe、Hidetsugu Wakabayashi、Kimio Shindo、Teruo Kurihara、Sumio Ishikawa、(the late) Masanori Kageyama

  DOI：10.1246/cl.1995.25

  日期：1995.1

  A very convenient, one-pot synthesis (in ca. 80% yield) of 3-Bromo-1,5- and -1,7-azulenequinones which can be used as synthones has been developed by polybromination of azulenes. Zink dust reduction and reductive acetylation of these azulenequinones were studied, and possible pathways for the present synthesis are briefly discussed.

  可用作合成酮的 3-Bromo-1,5- 和 -1,7-azulenequinones 的非常方便的一锅法合成（产率约 80%）已通过 azulenes 的多溴化而开发。研究了这些 azulequinones 的锌粉还原和还原乙酰化，并简要讨论了本合成的可能途径。
• Photodimerizations of 1,5- and 1,7-Azulenequinones: Solvent, Substituent, and Concentration Effects on the Product Distribution
  作者：Hiroko Kawakami、Yong Zhe Yan、Nobuo Kato、Akira Mori、Hitoshi Takeshita、the late Tetsuo Nozoe

  DOI：10.1246/bcsj.71.711

  日期：1998.3

  with a high-pressure mercury lamp. In polar solvents, head-to-head dimers were predominant, whereas head-to-tail dimers increased in less polar solvents. From 3-methoxy-1,5-azulenequinone, four products were obtained, while bromoazulenequinones and 1,5-azulenequinone gave a single dimer. The product distribution was dependent on the polarity of solvents, substituents, and concentrations.

  Azulenequinones 在高压汞灯照射下会产生二聚体。在极性溶剂中，头对头二聚体占主导地位，而在极性较小的溶剂中头对尾二聚体增加。从 3-甲氧基-1,5- azulenequinone 得到四种产物，而溴代azulenequinones 和 1,5-azulenequinone 得到单一的二聚体。产物分布取决于溶剂的极性、取代基和浓度。
• Synthesis of 3-Bromo-1,5- and -1,7-Azulenequinones Having Some Alkyl or Phenyl Group by the Polybromination and Reductive Debromination of Their Bromo-Substituent
  作者：Tetsuo Nozoe、Hidetsugu Wakabayashi、Kimio Shindo、Masafumi Yasunami

  DOI：10.1246/cl.1995.439

  日期：1995.6

  2-Methyl-, 2-phenyl-, 5- and 6-isopropylazulenes, and 5-isopropyl- and 6-isopropyl-2-methylazulenes were led to the corresponding 1,5- and 1,7-azulenequinones by polybromination in aqueous THF. 1-Carboxylic acid derivatives of these alkylazulenes also gave same products. Three isomeric 2-methyl derivatives of 3,3-biazulenequinones were produced from 2-methylazulene as minor products. Treatment of

  2-甲基-, 2-苯基-, 5- 和 6-异丙基 azulenes, 和 5-isopropyl- 和 6-isopropyl-2-methylazulenes 在四氢呋喃水溶液中通过多溴化反应生成相应的 1,5- 和 1,7-azulenequinones . 这些烷基甘菊烯的 1-羧酸衍生物也得到相同的产物。3,3-biazulenequinones 的三种异构 2-甲基衍生物作为次要产物由 2-methylazulene 生产。在乙酸中用锡粉处理溴代芴醌，得到相应的母体醌。
• Novel Non-benzenoid Electron Acceptors: Syntheses and Electron Acceptability of Tetracyanoazulenequinodimethanes and Dicyanoazulenequinonemethides
  作者：Ohki Sato、Yosuke Koizumi、Yoshihiro Sekiguchi、Sachiko Yoshioka、Josuke Tsunetsugu、Yong Zhe Yan、Akira Mori、Hitoshi Takeshita、Tetsuo Nozoe

  DOI：10.1246/cl.2000.1078

  日期：2000.9

  Tetracyanoazulenequinodimethanes and dicyanoazulenequinonemethides, a new family of azulene-based electron acceptors have been derived from mono-, di-, and tri-bromo- and -chloro-azulenequinones by reaction with titanium tetrachloride, malononitrile and pyridine. Their unique electron acceptability has been revealed by CV measurement.

  四氰基苊并喹啉二甲烷和二氰基苊并喹啉甲肟是苊类电子受体的新家族，由单溴、二溴和三溴苊并喹啉酮与四氯化钛、丙二腈和吡啶反应生成。通过CV测量，揭示了它们独特的电子接受能力。