2,6-di-tert-butyl-4-phenylphenoxyl | 2525-38-4

• 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: 2,6-di-tert-butyl-4-phenylphenoxyl
• 英文别名: 2,6-di-t-butyl-4-phenylphenoxyl；3,5-Di-tert-butyl-biphenyl-4-yloxyl；4-Phenyl-2,6-Di-t-butyl-phenoxylradikal；4-Phenyl-2,6-di-t-butylphenoxylradikal；4-Phenyl-2,6-di-tert-butyl-pheoxyl-(1)
• CAS: 2525-38-4
• 化学式: C₂₀H₂₅O
• 分子量: 281.418
• InChiKey: PHLYBDYAEBALFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2,6-di-tert-butyl-4-phenylphenoxyl 在 sodium hydroxide 、 溴 、 苯 作用下， 生成 4-hydroxy-4-phenyl-2,6-di-t-butylcyclohexa-2,5-dienone
  参考文献：
  名称：

  Mueller et al., Chemische Berichte, 1959, vol. 92, p. 474,480

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-di(t-butyl)-4-phenylphenol 在 正丁基锂 作用下， 以 正己烷 、 苯 为溶剂， 生成 2,6-di-tert-butyl-4-phenylphenoxyl
  参考文献：
  名称：

  方便的单分子芳氧基基团I-芳氧基草酰氯

  摘要：

  易合成的芳氧基草酰氯半酯的紫外光解提供了一种新的单分子芳氧基自由基来源，如ESR和UV-vis光谱法所示。

  DOI：

  10.1016/s0040-4039(01)80721-8

文献信息

• Convenient unimolecular sources of aryloxyl radicals II — aryloxyoxalyl tert-butylperoxides
  作者：David A. Modarelli、Frank C. Rossitto、Paul M. Lahti

  DOI：10.1016/s0040-4039(01)80722-x

  日期：1989.1

  UV photolysis and mild thermolysis of aryloxyoxalyl tert-butylperoxides provides a new unimolecular source of aryloxyl radicals, as shown by ESR and UV-vis spectroscopy.

  紫外光分解和芳氧基草酰叔丁基过氧化物的温和热解提供了新的单分子芳氧基自由基来源，如ESR和UV-vis光谱所示。
• Mechanism of antioxidant reaction of vitamin E: charge transfer and tunneling effect in proton-transfer reaction
  作者：Shinichi Nagaoka、Aya Kuranaka、Hideki Tsuboi、Umpei Nagashima、Kazuo Mukai

  DOI：10.1021/j100185a065

  日期：1992.3

  In order to shed light on the mechanism of proton-transfer reactions, a kinetic and ab initio study of the antioxidant action (intermolecular proton transfer) of vitamin E derivatives has been carried out. The second-order rate constants (k(s)'s) for the reaction of tocopherols (TocH's) with variously substituted phenoxyl radicals (PhO.'s) in ethanol were measured with a stopped-flow spectrophotometer. The half-wave reduction potentials (E1/2's) of PhO.'s were obtained by using a cyclic voltammetry technique. The result indicates that k(s) increases as the total electron-donating capacity of the alkyl substituents at the aromatic ring of TocH or the electron-withdrawing capacity of the substituent of PhO. increases. k(s) for the reaction of deuterated tocopherol derivatives (TocD's) with a PhO. in deuterated ethanol (C2H5OD, ethanol-d1) was also measured. A substantial deuterium kinetic isotope effect on k(s) is observed. In the reactions of each PhO. with various TocH's, a plot of log k(s) vs peak oxidation potential (E(p)) of TocH is found to be linear. The slope of its plot for TocD's is clsoe to that for TocH's. In the reactions of each TocH with various PhO.'s, a plot of log k(s) vs E1/2 of PhO. is found to be linear. The geometries of TocH's were optimized with the semiempirical modified neglect of diatomic overlap (MNDO) method. The Koopmans' theorem first ionization energies (IP) for those geometries were calculated with the ab initio method. In the reactions of a PhO. with various TocH's, plots of log k(s) vs IP, the activation energy (E(act)) vs IP, and E(p) vs IP are also found to be linear. From these results, it is considered that both the charge transfer and the proton tunneling play important roles in the antioxidant reaction of TocH. The transition state has the property of the charge-transfer species. The proton tunneling takes place below the transition state. Tunneling allows the proton to cut a corner on the potential energy surface. Our explanation will be widely applicable to many proton-transfer reactions.
• Mueller,E. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 645, p. 1 - 18
  作者：Mueller,E. et al.

  DOI：——

  日期：——
• Reaction of stannous bis-3,6-di-tert-butyl-o-semiquinolate with phenoxyl radicals
  作者：R. R. Rakhimov、P. M. Solozhenkin、V. S. Pupkov、A. I. Prokof'ev

  DOI：10.1007/bf00957843

  日期：1990.7

  An EPR study was carried out on the reaction of stannous bis-3,6-di-tert-butyl-o-semiquinolate with several phenoxyl radicals. An oxidative addition reaction may proceed with the formation of radicals with stannic ions. The reaction of biradical stannous complexes with 3,6-di-tert-butyl-2-hydroxyphenoxyl in the presence of triphenylphosphine in toluene gave a tin-containing free radical. The EPR spectra of this radical indicated rapid interligand exchange of the unpaired electron and bond.
• Convenient unimolecular sources of aryloxyl radicals I -- aryloxyoxalyl chlorides
  作者：David A. Modarelli、Frank C. Rossitto、Paul M. Lahti

  DOI：10.1016/s0040-4039(01)80721-8

  日期：1989.1

  UV photolysis of readily synthesized aryloxyoxalyl chloride half-esters provides a new unimolecular source of aryloxyl radicals, as shown by ESR and UV-vis spectroscopy.

  易合成的芳氧基草酰氯半酯的紫外光解提供了一种新的单分子芳氧基自由基来源，如ESR和UV-vis光谱法所示。