phloroglucinol radical | 154848-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: phloroglucinol radical
• 英文别名: phloroglucinol；3,5-dihydroxy-phenyloxyl；Phloroglucinradikal
• CAS: 154848-77-8
• 化学式: C₆H₅O₃
• 分子量: 125.104
• InChiKey: WTSPLBNXBKPBKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  间苯三酚 在 1,1-二苯-2-苦基肼 作用下， 以 苯 为溶剂， 生成 phloroglucinol radical
  参考文献：
  名称：

  介质极性对非质子溶剂中羟基苯与肼基反应机理的影响

  摘要：

  通过实验和量子化学方法阐明了二羟基苯和三羟基苯与2,2'-二苯基-1-吡啶并肼基（稳定基团）在不同极性的非质子介质中的反应机理。已经确定了反应的动力学，化学计量和活化参数。在苯（非极性溶剂）中，所研究的反应是通过氢原子转移机理发生的。在电离能力弱的极性溶剂（即DMSO）中，反应主要是通过电子和质子转移的更快机理进行的。

  DOI：

  10.1134/s1070363217040053

文献信息

• Stopped-Flow and Spectrophotometric Study on Radical Scavenging by Tea Catechins and the Model Compounds.
  作者：Yasushi SENBA、Tsukasa NISHISHITA、Keiko SAITO、Hiroe YOSHIOKA、Hisashi YOSHIOKA

  DOI：10.1248/cpb.47.1369

  日期：——

  Radical scavenging of four tea catechins, (-)-epicatechin (EC), (-)-epigallocatechin (EGC), (-)-epicatechin gallate (ECg) and (-)-eppigallocatechin gallate (EGCg), and the model compounds of their partial structure was examined against the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical using stopped-flow and spectrophotometric methods. The number of DPPH radicals scavenged by a polyphenol molecule was larger than that of phenolic hydroxyl groups, suggesting that hydrogens which bond directly to the aromatic ring can also participate in radical scavenging. A model for the scavenging reaction was proposed in which the reaction proceeded with successive dehydrogenation from a polyphenol molecule. Analysis of the second order reaction rate constants and the activation parameters between DPPH and polyphenol at the early stage of the reaction showed that the values depended on the number of phenolic hydroxyl groups and their mutual position. Contribution of the A ring of catechins to the rate constants was estimated to be far smaller than that from the B ring. In the EGCg molecule, the B ring and the gallate group were not independent, but acted as a single group for DPPH radical scavenging.

  对四种茶多酚(-)-表儿茶素(EC)、(-)-表没食子儿茶素(EGC)、(-)-表儿茶素没食子酸酯(ECg) 和(-)-表没食子儿茶素没食子酸酯(EGCg)及其部分结构的模型化合物， 用停流法和分光光度法研究了它们对1,1-二苯基-2-苦基肼基(DPPH)自由基的清除作用，发现一个多酚分子清除DPPH自由基的能力比羟基的数目强，说明直接与芳香环相连的氢原子也能参与自由基清除反应。提出了一个多酚分子连续脱氢的清除反应模型。研究了早期反应阶段DPPH和多酚的二级反应速率常数和活化参数，发现其数值与酚羟基数目及其相对位置有关。儿茶素A环对速率常数的贡献比B环小得多。在EGCg分子中，B环和没食子酸基团不是独立的，而是作为一个整体对DPPH自由基起清除作用。
• O–H Bond dissociation enthalpies in hydroxyphenols. A time-resolved photoacoustic calorimetry and quantum chemistry study
  作者：Catarina F. Correia、Rita C. Guedes、Rui M. Borges dos Santos、Benedito J. Costa Cabral、José A. Martinho Simões

  DOI：10.1039/b314093h

  日期：——

  Time-resolved photoacoustic calorimetry (TR-PAC) was used to investigate the energetics of O–H bonds of phenol, catechol, pyrogallol, and phloroglucinol. Values of −27.1 ± 3.9, −44.1 ± 4.4 and −1.6 ± 3.8 kJ mol−1, respectively, were obtained for the solution-phase (acetonitrile) O–H bond dissociation enthalpies of the last three compounds relative to the O–H bond dissociation enthalpy in phenol, ΔD

  时间分辨光声量热法 (TR-PAC) 用于研究苯酚、儿茶酚、邻苯三酚和间苯三酚的 O-H 键的能量学。最后三种化合物相对于 O-H 的溶液相（乙腈）O-H 键解离焓分别为 -27.1 ± 3.9、-44.1 ± 4.4 和 -1.6 ± 3.8 kJ mol-1。苯酚中的键解离焓，ΔDHosln(ArO-H) = DHosln(ArO-H) - DHosln(PhO-H)。乙腈中的 PhO-H 键解离焓确定为 388.7 ± 3.7 kJ mol-1。进行密度泛函理论 (MPW1PW91/aug-cc-pVDZ) 计算和完整基组 (CBS-4M) 计算以分析分子内氢键并预测气相 O-H 键解离焓 DHo(ArO-H) . 基于 DFT 计算的微溶剂化模型，用于研究苯酚及其自由基在乙腈中的差异溶剂化，并桥接溶液和气相数据。结果强烈表明 ΔDHosln(ArO–H) ≈ ΔDHo(ArO–H)
• Wang, Degui; Gyoergy, Istvan; Hildenbrand, Knut, Journal of the Chemical Society. Perkin transactions II, 1994, # 1, p. 45 - 56
  作者：Wang, Degui、Gyoergy, Istvan、Hildenbrand, Knut、Sonntag, Clemens von

  DOI：——

  日期：——
• One-electron redox reactions in aqueous solutions of sulfite with hydroquinone and other hydroxyphenols
  作者：Robert E. Huie、P. Neta

  DOI：10.1021/j100264a032

  日期：1985.8