2-Ethoxy-3,5,6-trichlor-1,4-benzochinon | 58965-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Ethoxy-3,5,6-trichlor-1,4-benzochinon
• 英文别名: 2,3,5-Trichloro-6-ethoxycyclohexa-2,5-diene-1,4-dione
• CAS: 58965-69-8
• 化学式: C₈H₅Cl₃O₃
• 分子量: 255.485
• InChiKey: KKIFFBMQNIUXIK-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  347.7±42.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-Ethoxy-3,5,6-trichlor-1,4-benzochinon 在 氢氧化钾 作用下， 生成 氯冉酸
  参考文献：
  名称：

  Berlin,A.Ya.; Makarova,A.N., Journal of general chemistry of the USSR, 1960, vol. 30, p. 1587 - 1590

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium ethanolate 、 四氯苯醌 以 乙醇 为溶剂， 反应 12.0h， 以68%的产率得到2-Ethoxy-3,5,6-trichlor-1,4-benzochinon
  参考文献：
  名称：

  磺胺甲恶唑与新型2,3,5-三氯-6-烷氧基-1,4-苯醌分子配合物形成的光谱研究

  摘要：

  摘要 UV-Vis、1H NMR、FT-IR、LC-MS和荧光光谱技术被用来研究磺胺甲恶唑与烷氧基取代的2,3,5-三氯-1,4-苯醌相互作用的机理并表征反应产品。发现这些醌与磺胺甲恶唑 (SULF) 的相互作用是通过供体-受体复合物的形成进行的，其中包含自由基阴离子并将其转化为产物。荧光猝灭研究表明供体和受体之间的相互作用是自发的。CT 复合物的缔合常数与 Taft 的极性和空间常数的相关性表明极性因子在控制反应性中起重要作用。

  DOI：

  10.1016/j.molstruc.2012.09.062

文献信息

• Synthesis and characterization of molecular complexes of cimetidine with water soluble 1,4-benzoquinones
  作者：C. Balraj、A. Satheshkumar、K. Ganesh、E.H. El-Mossalamy、K.P. Elango

  DOI：10.1016/j.molstruc.2013.07.025

  日期：2013.10

  Abstract The molecular complexes of novel water soluble 1,4-benzoquinones possessing different alkoxy substituents, with cimetidine drug have been investigated using various spectral techniques such as UV–Vis, 1 H NMR, FT-IR. The stoichiometry of the CT complexes was found to be 1:1, in all the cases. The Density Functional Theory calculations supported the experimental observations. Correlation of

  摘要 具有不同烷氧基取代基的新型水溶性 1,4-苯醌与西咪替丁药物的分子复合物已使用各种光谱技术进行了研究，例如 UV-Vis、1 H NMR、FT-IR。在所有情况下，发现 CT 复合物的化学计量比为 1:1。密度泛函理论计算支持实验观察。CT 配合物的形成常数 ( K ) 与 Taft 的极性 ( σ ⁎ ) 和空间 ( E s ) 常数的相关性表明，烷氧基的电子释放特性的增加使这些受体越来越弱，而取代基降低了形成常数。
• Conversion of Pentahalogenated Phenols by Microperoxidase-8/H₂O₂ to Benzoquinone-Type Products
  作者：Ahmed M. Osman、Maarten A. Posthumus、Cees Veeger、Peter J. van Bladeren、Colja Laane、Ivonne M. C. M. Rietjens

  DOI：10.1021/tx980037l

  日期：1998.11.1

  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.
• Spectral and theoretical studies on the molecular complexes of azacyclonol with new π-acceptors, alkoxysubstituted 1,4-benzoquinones
  作者：C. Balraj、A. Satheshkumar、K. Ganesh、Kuppanagounder P. Elango

  DOI：10.1016/j.molstruc.2012.09.033

  日期：2013.3

  The molecular complexes of a series of new electron acceptors, 1,4-benzoquinones possessing variety of alkoxy substituents, with azacyclonol have been investigated using various spectral techniques such as UV-Vis, H-1 NMR, FT-IR, fluorescence and LC-MS. The stoichiometry of the complexes was determined by Job's continuous variation method and was found to be 1:1, in all the cases. The results of equilibrium, and kinetic studies were well supported by ab initio DFT calculations. Correlation of formation constants of the complexes with Taft's polar and steric constants indicated that both these factors play significant role in governing the reactivity. Also, the results indicated that an increase in electron releasing property of the alkoxy group makes these acceptors increasingly weaker while an increase in steric property of the substituent decreased the formation constant. (c) 2012 Elsevier B.V. All rights reserved.
• Kallmayer; Fritzen, Pharmazie, 1994, vol. 49, # 4, p. 235 - 238
  作者：Kallmayer、Fritzen

  DOI：——

  日期：——
• US4042764A
  申请人：——

  公开号：US4042764A

  公开（公告）日：1977-08-16