2-(4-carboxyphenyl)-3,6-dichloro-2,5-cyclohexadiene-1,4-dione | 147932-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-carboxyphenyl)-3,6-dichloro-2,5-cyclohexadiene-1,4-dione
• 英文别名: 2-(Carboxyphenyl)-3,6-dichloro-1,4-benzoquinone；4-(2,5-Dichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)benzoic acid
• CAS: 147932-80-7
• 化学式: C₁₃H₆Cl₂O₄
• 分子量: 297.094
• InChiKey: HOVZMWJHNZEVFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  484.4±45.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二氯-1,4-苯醌 、 培美曲塞二钠杂质14 生成 2-(4-carboxyphenyl)-3,6-dichloro-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  光诱导的电子转移，用于高潜力的醌敏化剂和噻吩。噻吩自由基阳离子被水捕获的速率

  摘要：

  报道了氯化苯醌三重态的电子转移性质，包括瞬态光谱和供体噻吩对电子转移的猝灭速率。已经测量了水捕获噻吩基的速率常数。

  DOI：

  10.1016/s0040-4039(00)60564-6

文献信息

• Electron-transfer photochemistry of thianthrene. Nucleophile-assisted photooxidation to sulfoxide
  作者：Guilford Jones、Bin Huang、Susan F. Griffin

  DOI：10.1021/jo00060a016

  日期：1993.4

  The photochemistry of thianthrene (1) in the presence of a variety of electron acceptors in acetonitrile/water has been investigated. Diffusion-limited rates of fluorescence quenching were observed on excitation of 1 (with fumaronitrile and with methyl phthalate). Alternatively, addition of 1 led to quenching of the fluorescence emission of ketones, biacetyl, and fluorenone and to the quenching of the excited triplet states of quinones such as 2,5-dichloro-p-benzoquinone (5) and 9,10-anthraquinone (3). Steady irradiation of 1 with selected acceptors results in photooxidation yielding the sulfoxide (2) and the expected photoreduction products. The electron-transfer mechanisms were further studied by laser flash photolysis. The quenching of ketone triplets by 1 resulted in formation of the radical cation of 1 (lambda(max) 540 nm). The decay of this species and its dependence on the concentration of water present were determined; the bimolecular rate constant for trapping of 1'+ by water in acetonitrile-water solutions is 4.9 x 10(4) m-1 s-1 under conditions in which 5 acts as a sensitizer. The nucleophilic trapping of the 1 radical cation by imidazole (k = 3.6 x 10(7) m-1 s-1) was also investigated. The mechanism of photoinduced two-electron oxidation of 1 and the role played by nucleophiles in facilitating the reaction are discussed in detail.