trifluoroethoxy-p-benzoquinone | 57123-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trifluoroethoxy-p-benzoquinone
• 英文别名: Ethoxytrifluor-p-benzoquinon
• CAS: 57123-50-9
• 化学式: C₈H₅F₃O₃
• 分子量: 206.121
• InChiKey: DZDVZPYDUDHFDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙醇 、 四氟对苯醌 在 双氧水 作用下， 以 水 为溶剂， 反应 1.0h， 生成 trifluoroethoxy-p-benzoquinone 、 3,4,6-trifluoro-5-hydroxycyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  Conversion of Pentahalogenated Phenols by Microperoxidase-8/H₂O₂ to Benzoquinone-Type Products

  摘要：

  This study reports the microperoxidase-8 (MP8)/H2O2-catalyzed dehalogenation of pentafluorophenol and pentachlorophenol, compounds whose toxic effects and persistence in the environment are well documented. The primary products of this dehalogenation reaction appear to be the corresponding tetrahalo-p-benzoquinones. Under the conditions used, the fluorinated phenol and its intermediate products are more susceptible to degradation than the corresponding chlorinated analogue and its products. The main degradation products of tetrachloro-p-benzoquinone and tetrafluoro-p-benzoquinone were identified as trichlorohydroxy-p-benzoquinone and trifluorohydroxy-p-benzoquinone, respectively. This secondary conversion of tetrafluoro-p-benzoquinone and tetrachloro-p-benzoquinone was not mediated by MP8, but was driven by H2O2. Evidence is presented for a mechanism where H2O2 molecules and not hydroxide anions are the reactive nucleophilic species attacking the tetrahalo-p-benzoquinones. In addition to the formation of the trihalohydroxy-p-benzoquinones, the formation of adducts of the tetrahalo-p-benzoquinone products with ethanol, present in the incubation medium, was observed. The adduct from the reaction of tetrachloro-p-benzoquinone with ethanol was isolated and identified as trichloroethoxyquinone. Thus, the present paper describes a system in which the formation of tetrahalo-p-benzoquinone-type products by an oxidative heme-based catalyst could be unequivocally demonstrated.

  DOI：

  10.1021/tx980037l