2,3,4,5,6-Pentachlor-4-pentachlorphenoxy-cyclohexa-2,5-dien-1-on | 17540-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,4,5,6-Pentachlor-4-pentachlorphenoxy-cyclohexa-2,5-dien-1-on
• 英文别名: (1,2,3,5,6-Pentachlor-4-oxo-cyclohexa-dien-yl)-(pentachlor-phenyl)-ether, dimeres Pentachlor-phenoxyl；2,3,4,5,6-Pentachloro-4-pentachlorophenoxy-2,5-cyclohexadienone；2,3,4,5,6-pentachloro-4-(2,3,4,5,6-pentachlorophenoxy)cyclohexa-2,5-dien-1-one
• CAS: 17540-48-6
• 化学式: C₁₂Cl₁₀O₂
• 分子量: 530.661
• InChiKey: OANPRAMHZJYQSU-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  551.0±50.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-Pentachlor-4-pentachlorphenoxy-cyclohexa-2,5-dien-1-on 以 乙酸乙酯 为溶剂， 反应 24.0h， 以87.1%的产率得到四氯苯醌
  参考文献：
  名称：

  Primary Product of the Horseradish Peroxidase-Catalyzed Oxidation of Pentachlorophenol

  摘要：

  Peroxidases are a class of enzymes that catalyze the oxidation of various phenolic substrates by hydrogen peroxide. They are common enzymes in soil and are also available commercially, so that they have been proposed as agents of phenolic pollutant transformation both in the environment and in engineered systems. Previous research on the peroxidase-catalyzed oxidation of pentachlorophenol (PCP) has suggested that tetrachloro-p-benzoquinone (chloranil) is the principal product and that a considerable fraction of the PCP added to reaction mixtures appears to be resistant to oxidation. In experiments employing alternative methods of product separation and analysis, we found that both of these observations a re artifacts of extraction and analytical methods used in previous studies. The major product of the horseradish peroxidase-catalyzed oxidation of pentachlorophenol from pH 4-7 was 2,3,4,5,6-pentachloro-4-pentachlorophenoxy-2,5-cyclohexadienone (PPCHD), (PPCHD), which is formed by the coupling of two pentachlorophenoxyl radicals. The yield of chloranil and other soluble products was negligible. PPCHD is insoluble and unreactive in aqueous media but is reactive when dissolved in various organic solvents. Substantial amounts of chloranil were formed when PPCHD was dissolved in benzene, ethyl acetate, or methanol; less was formed in hexane and acetonitrile; and negligible amounts were formed in dimethylformamide. High-pressure liquid chromatography (HPLC) analysis of PPCHD indicated that it is capable of undergoing dissociation and reduction to pentachlorophenol under typical reversed-phase HPLC conditions. Chlorinated oligomeric products are formed when PPCHD is stored in acetonitrile, either alone or with added pentachlorophenol. Our results demonstrate that the removal of PCP in peroxidase-catalyzed reactions can be much higher than indicated in previous work, as long as the initial product is separated by filtration or other physical means.

  DOI：

  10.1021/es981126n
• 作为产物：
  描述：

  五氯酚 在 硝酸 作用下， 以 various solvent(s) 为溶剂， 生成 2,3,4,5,6-Pentachlor-4-pentachlorphenoxy-cyclohexa-2,5-dien-1-on
  参考文献：
  名称：

  Primary Product of the Horseradish Peroxidase-Catalyzed Oxidation of Pentachlorophenol

  摘要：

  Peroxidases are a class of enzymes that catalyze the oxidation of various phenolic substrates by hydrogen peroxide. They are common enzymes in soil and are also available commercially, so that they have been proposed as agents of phenolic pollutant transformation both in the environment and in engineered systems. Previous research on the peroxidase-catalyzed oxidation of pentachlorophenol (PCP) has suggested that tetrachloro-p-benzoquinone (chloranil) is the principal product and that a considerable fraction of the PCP added to reaction mixtures appears to be resistant to oxidation. In experiments employing alternative methods of product separation and analysis, we found that both of these observations a re artifacts of extraction and analytical methods used in previous studies. The major product of the horseradish peroxidase-catalyzed oxidation of pentachlorophenol from pH 4-7 was 2,3,4,5,6-pentachloro-4-pentachlorophenoxy-2,5-cyclohexadienone (PPCHD), (PPCHD), which is formed by the coupling of two pentachlorophenoxyl radicals. The yield of chloranil and other soluble products was negligible. PPCHD is insoluble and unreactive in aqueous media but is reactive when dissolved in various organic solvents. Substantial amounts of chloranil were formed when PPCHD was dissolved in benzene, ethyl acetate, or methanol; less was formed in hexane and acetonitrile; and negligible amounts were formed in dimethylformamide. High-pressure liquid chromatography (HPLC) analysis of PPCHD indicated that it is capable of undergoing dissociation and reduction to pentachlorophenol under typical reversed-phase HPLC conditions. Chlorinated oligomeric products are formed when PPCHD is stored in acetonitrile, either alone or with added pentachlorophenol. Our results demonstrate that the removal of PCP in peroxidase-catalyzed reactions can be much higher than indicated in previous work, as long as the initial product is separated by filtration or other physical means.

  DOI：

  10.1021/es981126n

文献信息

• Beiträge zur chemie des iodpentafluorids. Teil I. Iod(V)-verbindungen mit monofunktionellen alkoholaten
  作者：Herman Josef Frohn、Wolfgang Pahlmann

  DOI：10.1016/s0022-1139(00)85206-9

  日期：1984.2

  The behavior of iodine pentafluoride towards nucleophilic exchange of fluoride against monofunctional alcoholates in aprotic media is investigated using silylated methanol, isopropanol, tertiary butanol, phenol, alkylated phenol, and pentachlorophenol as educts. 19F-NMR-spectroscopic and preparative details are given for iodine(V)-fluoride- methanolates and fluoride-oxides. Dismutation, elimination

  使用硅烷化的甲醇，异丙醇，叔丁醇，苯酚，烷基化苯酚和五氯苯酚作为离析物，研究了五氟化碘对氟在质子惰性介质中与单官能醇化物进行氟化物亲核交换的行为。给出了碘（V）-氟化物-甲醇化物和氟化物氧化物的19 F-NMR光谱学和制备细节。据报道涉及碘（V）-醇盐和氟化芳基氧化物的歧化，消除和氧化还原反应。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.8, 2.4, page 2 - 54
  作者：

  DOI：——

  日期：——
• Synthesis of nonachloro-4-phenoxyphenol
  作者：Jo Anne B. Campbell、Max L. Deinzer、Terry L. Miller、Douglas C. Rohrer、Phyllis E. Strong

  DOI：10.1021/jo00146a027

  日期：1982.12
• Budnik, A. G.; Shteingarts, V. D.; Yakobson, G. G., Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 1204 - 1212
  作者：Budnik, A. G.、Shteingarts, V. D.、Yakobson, G. G.

  DOI：——

  日期：——
• Fort, Annales de Chimie (Cachan, France), 1959, vol. <13> 4, p. 203,239
  作者：Fort

  DOI：——

  日期：——