3-bromo-2-methoxy-1,5-azulenequinone | 189197-53-3

• 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-2-methoxy-1,5-azulenequinone
• 英文别名: 3-Bromo-2-methoxyazulene-1,5-dione
• CAS: 189197-53-3
• 化学式: C₁₁H₇BrO₃
• 分子量: 267.079
• InChiKey: SRQUAAUDWKPYDP-UHFFFAOYSA-N

物化性质

• 沸点：
  480.5±45.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙胺 、 3-bromo-2-methoxy-1,5-azulenequinone 以45%的产率得到3-(Ethylamino)-2-methoxyazulene-1,5-dione
  参考文献：
  名称：

  Synthesis of Heterocycle-annulated Azulenequinone Derivatives

  摘要：

  Treatment of 2-methoxyazulene (2) with 4.2 equiv. of bromine in aqueous THF at 0degreesC for 1 h afforded 3-bromo-2-methoxy-1,5- (1a) and -1,7-azulenequinone (1b) in a 16:1 ratio. Reaction of 1a with o-aminobenzenethiols gave 12H-azuleno[1,2-b]benzo[e][1,4]thiazine-7,11-dione derivatives (6a,b).

  DOI：

  10.3987/com-01-s(k)32
• 作为产物：
  描述：

  2-methoxyazulene 在 水 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 3-bromo-2-methoxy-1,5-azulenequinone 、 3-bromo-2-methoxy-1,7-azulenequinone
  参考文献：
  名称：

  Formation of Azulenequinone Derivatives from Variously Functionalized Azulenes by Bromine-oxidation

  摘要：

  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.

  DOI：

  10.1002/jccs.199700002