4-苯基苯氧基 | 35645-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-苯基苯氧基
• 英文名称: 4-phenylphenoxyl radical
• CAS: 35645-18-2
• 化学式: C₁₂H₉O
• 分子量: 169.203
• InChiKey: WXZUDQSXINZYKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-苯基苯氧基 在 氧气 作用下， 以 乙腈 为溶剂， 生成 对羟基联苯
  参考文献：
  名称：

  4-乙酰氧基-4-芳基-2,5-环己二烯酮光解过程中产生的反应中间体的表征：氧鎓离子和芳氧基自由基

  摘要：

  Aryloxenium 离子 1 是反应性中间体，与更为人所知的芳基碳离子和芳基氮离子等电子。它们被提议参与合成和工业上有用的酚类氧化反应。然而，这些中间体的机理研究是有限的。直到最近，这些中间体在溶液中的寿命及其反应模式还是未知的。以前，羟基喹啉酯 2 已被用于生成 1，在黑暗中的水解反应过程中，通过叠氮化物离子捕获间接检测到生成叠氮化物加合物 4，但会消耗醌醇 3。在水溶液中存在 O(2) 的情况下，2b 的激光闪光光解 (LFP) 导致两种反应性中间体分别具有 lambda(max) 360 和 460 nm，而在纯 CH(3)CN 中只有一种具有 lambda( max) 350 nm 产生。λ(max) 460 nm 的中间体先前基于在 N(3)(-) 存在下对其分解动力学的直接观察，与水解反应的叠氮化物离子捕获结果和光解反应产物的比较而被鉴定为 1b（ 3b)。1b 的计算 (B3LYP/6-31G(d))

  DOI：

  10.1021/ja805336d
• 作为产物：
  描述：

  对羟基联苯 在 [α-SiV(V)W11O40]K5*7H2O 作用下， 以 acetate buffer 为溶剂， 生成 4-苯基苯氧基
  参考文献：
  名称：

  使用多金属氧酸盐作为酚氧化酶活性的仿生模型氧化酚

  摘要：

  取代基氧化的动力学研究 酚类与任一钒（V）polyoxotungstate，[α-SIV V w ^ 11 ö 40 ] 5-（即硅钨酸11 V），或锰（III）polyoxotungstate，[α-硅锰III W¯¯ 11（H 2 O）O- 39 ] 5-（即硅钨酸11的Mn），已经进行了。因为多金属氧酸盐SiW 11 V和SiW 11 Mn化合物的氧化还原电位，即。POM为0.67和0.76 V /NHE以及酚醛底物的电压分别在0.4-0.9 V /NHE 在 水，所产生的氧化反应是外能的或轻微的内能的。的反应性氧化作用 的替代 酚类通过SiW 11 V，在50°C的缓冲水溶液（pH = 4）中，发现与取代基的σ +参数相关，产生与电子共振的冈本-布朗ρ值（即-3.1）决定速率的电子转移途径的要求。的微不足道的价值溶剂用SiW 11 V氧化p -MeO-苯酚获得动力学同位素效应（k H

  DOI：

  10.1039/b703178e

文献信息

• Reaction of tert-butoxy radicals with phenols. Comparison with the reactions of carbonyl triplets
  作者：P. K. Das、M. V. Encinas、S. Steenken、J. C. Scaiano

  DOI：10.1021/ja00404a030

  日期：1981.7

  Tert-butoxy radicals generated in the photodecomposition of di-tert-butyl peroxide react efficiently with phenols to yield the corresponding phenoxy radicals. Typical rate constants in benzene at 22/sup 0/C are 3.3 x 10/sup 8/ and 1.6 x 10/sup 9/ M/sup -1/ s/sup -1/ for phenol and p-methoxyphenol, respectively. The process is considerably slower in polar solvents; e.g., when pyridine is used as cosolvent

  二叔丁基过氧化物光分解中产生的叔丁氧基自由基与酚类有效反应生成相应的苯氧基自由基。苯中的典型速率常数在 22/sup 0/C 时分别为 3.3 x 10/sup 8/ 和 1.6 x 10/sup 9/ M/sup -1/ s/sup -1/ 苯酚和对甲氧基苯酚。该过程在极性溶剂中要慢得多；例如，当使用吡啶作为助溶剂时，苯酚的速率常数下降到 4.1 x 10/sup 6/ M/sup -1/ s/sup -1/，这是由于强氢键降低了酚类 OH 的反应性团体。同位素效应 (H/D) 通常在 3 到 5 的范围内。5个数字，4个表格。
• Direct Irradiation of Phenol and <i>Para</i>-Substituted Phenols with a Laser Pulse (266 nm) in Homogeneous and Micro-heterogeneous Media. A Time-Resolved Spectroscopy Study
  作者：Gastón Siano、Stefano Crespi、Sergio M. Bonesi

  DOI：10.1021/acs.joc.0c02031

  日期：2020.11.6

  Direct irradiation of para-substituted phenols under N2 atmosphere in homogeneous (cyclohexane, acetonitrile, and methanol) and micellar (SDS) solution was investigated by means of time-resolved spectroscopy. After a laser pulse (266 nm), two transient species were formed, viz. the para-substituted phenol radical-cations and the corresponding phenoxy radicals. The radical-cations showed a broad absorption

  通过时间分辨光谱法研究了N 2气氛下均相（环己烷，乙腈和甲醇）和胶束（SDS）溶液中对位取代的苯酚的直接辐照。在激光脉冲（266 nm）之后，形成了两个瞬态物质，即。的对位取代的酚自由基阳离子和相应的苯氧自由基。自由基阳离子在390至460 nm之间显示出较宽的吸收带，而苯氧基自由基在320 nm和400–410 nm处具有两个特征带。自由基阳离子的去质子化速率常数（k H）为10 5 s –1和苯氧基自由基的反应速率常数（kR）的阶数为10 9 –10 10 M –1 ·s –1。所述ķ ħ速率常数给出了良好的线性相关性哈米特具有正斜率表明吸电子取代基增强自由基阳离子的酸度。的结合常数（ķ b的的）对位还测量了用表面活性剂取代的酚，NOESY实验表明酚位于胶束的疏水核中。最后，计算计算提供了瞬态的预测吸收光谱，并且在这些物种的较低吸收带的理论能量和实验能量之间获得了良好的线性相关性。
• Quantitative Model of the Enhancement of Peroxidase-Induced Luminol Luminescence
  作者：Patricia M. Easton、Adrian C. Simmonds、Askar Rakishev、Alexey M. Egorov、Luis P. Candeias

  DOI：10.1021/ja9605073

  日期：1996.1.1

  Many phenolic compounds are known to enhance the chemiluminescence associated with the horseradish peroxidase-catalyzed oxidation of luminol, but the mechanism of enhancement is still unproved. Using stopped-flow spectrophotometry, we have found that a series of luminescence enhancers react rapidly with the peroxidase reactive intermediates (compound I and compound II) supporting the hypothesis that the enhancement is due to the acceleration of the enzyme turnover. In addition, pulse radiolysis experiments have shown that the enhancers' phenoxyl radicals oxidize luminol, consistent with a redox mediator role for the enhancers. The latter reaction was found to be reversible, showing that enhancers of low reduction potential, which are efficient in accelerating the enzyme turnover, are also scavengers of luminol radicals and therefore luminescence quenchers. Using these data, a simple model is proposed which correctly predicts that the efficiency of a phenolic compound as luminescence enhancer depends on the reduction potential of the respective phenoxyl radical according to a bell-shaped function with a maximum at similar to 0.8 V.
• Two Channels of Electron Transfer Observed for the Reaction of <i>n</i>-Butyl Chloride Parent Radical Cations with Naphthols and Hydroxybiphenyls
  作者：H. Mohan、R. Hermann、S. Naumov、J. P. Mittal、O. Brede

  DOI：10.1021/jp9808431

  日期：1998.7.1

  Pulse radiolysis of naphthols (NpOH) and hydroxybiphenyls (ByOH) in n-butyl chloride (BuCl) at room temperature exhibits electron transfer at a bimolecular rate constant of (1.0-2.8) x 10(10) dm(3) mol(-1) s(-1). The experiments reveal the direct formation of two types of transients: phenol type radical cations (NpOH.+, ByOH(.+)) and phenoxyl type radicals (NpO., ByO(.)). This is explained by a mechanism involving two different electron-transfer channels. The solute radical cations exhibit two optical absorption bands in the 570-650 and 360-460 nm regions and undergo electron transfer with triethylamine and proton transfer with ethanol with bimolecular rate constants of (4-12) x 10(9) and (3-6) x 10(8) dm(3) mol(-1) s(-1), respectively. NpO. and ByO(.) have relatively long lifetimes and show absorption bands in the 340-400 and 470-540 nm regions. By way of comparison, these phenoxyl type radicals are separately generated by pulse radiolysis in aqueous alkaline solution containing sodium azide, i.e., by oxidation of the solutes with N-3(.) radicals. Under these conditions, the phenoxyl radicals decay by second-order kinetics with 2k = (1.2-4.5) x 10(8) dm(3) mol(-1) s(-1). The various modes of formation and decay of the phenolic radical cations are analyzed over a wide range of dose rate and solute concentrations: In comparison to radical cations of one-ring phenols, the increased stability of NpOH.+ and ByOH(.+) is explained by the delocalization of the positive charge over the whole aromatic system, a postulate supported by open-shell quantum chemical calulations.
• Influence of paramagnetic additives on the magnetic effect in the recombination of phenoxyl and semiquinone radicals in micelles
  作者：V. A. Kuz'min、P. P. Levin

  DOI：10.1007/bf00956620

  日期：1986.6