3-Chloroazulene-1,5-dione | 189197-57-7

• 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-Chloroazulene-1,5-dione
• CAS: 189197-57-7
• 化学式: C₁₀H₅ClO₂
• 分子量: 192.601
• InChiKey: DLRBIWSUYYJOEL-UHFFFAOYSA-N

物化性质

• 沸点：
  427.2±44.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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-Chloroazulene-1,5-dione 、 丙二腈 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 2-(3-Chloro-5-oxoazulen-1-ylidene)propanedinitrile 、 2-[3-Chloro-1-(dicyanomethylidene)azulen-5-ylidene]propanedinitrile
  参考文献：
  名称：

  Novel Non-benzenoid Electron Acceptors: Syntheses and Electron Acceptability of Tetracyanoazulenequinodimethanes and Dicyanoazulenequinonemethides

  摘要：

  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。

  DOI：

  10.1246/cl.2000.1078
• 作为产物：
  描述：

  1,3-二碘甘菊蓝 在 盐酸 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 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

文献信息

• Formation of Azulenequinone Derivatives from Variously Functionalized Azulenes by Bromine-oxidation
  作者：Paw-Wang Yang、Jhy-An Chen、Hidetsugu Wakabayashi、Kimio Shindo、Teruo Kurihara、Chi-Phi Wu、Masafumi Yasunami、The Late Tetsuo Nozoe

  DOI：10.1002/jccs.199700002

  日期：1997.2

  AbstractVariously functionalized 1,5‐ and 1,7‐azulenequinones were easily derived in one‐pot in 30‐50% yield from the bromine‐oxidation of 2‐methoxyazulene and 2‐methyl derivatives of 1‐cyano‐, 1‐methoxycarbonyl‐ and its 7‐isopropyl derivatives, while 1‐methoxycarbonylazulene afforded several unstable products from which we could not isolate any azulenequinones. 1‐Acetylazulene afforded 3‐bromo‐1,5‐ and ‐1,7‐azulenequinones via side‐chain brominated intermediates in high yield. 1,3‐Dichloroazulene afforded a mixture of 3‐chloro‐1,5‐ and −1,7‐azulenequinones, while 1‐fluoro‐ and 1,3‐diiodoazulene gave a mixture of 3‐bromoazulenequinones. Analogous oxidation of 1,3‐difluoroazulene produced 3‐fluoroazulenequinones, but we could not isolate them due to its instability. Hydroxy group of 2‐(3‐hydroxypropyl)azulene was intact during this quinone formation reaction.