4-(4'-bromophenyl)-2,6-di(t-butyl)phenol | 6257-24-5

• 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: 4-(4'-bromophenyl)-2,6-di(t-butyl)phenol
• 英文别名: 4'-Brom-3,5-di-tert.-butyl-4-hydroxy-biphenyl；4-(4-Bromophenyl)-2,6-ditert-butylphenol
• CAS: 6257-24-5
• 化学式: C₂₀H₂₅BrO
• 分子量: 361.322
• InChiKey: UQTKODOJHRWDAP-UHFFFAOYSA-N

物化性质

• 沸点：
  401.7±45.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(4'-nitrophenyl)-2,6-di-tert-butylphenol 在 palladium on charcoal copper(I) bromide 、 sodium nitrite 作用下， 以 乙醇 、 正己烷 、 正庚烷 、 硫酸 、 水 、 氢溴酸 、 乙酸乙酯 为溶剂， 生成 4-(4'-bromophenyl)-2,6-di(t-butyl)phenol
  参考文献：
  名称：

  Anti-inflammatory method

  摘要：

  2,6-二(叔丁基)苯酚在4位被一个具有宝贵药理活性的、可选地被取代的苯基基团所取代的化合物，作为抗炎剂。

  公开号：

  US04172151A1

文献信息

• Rieker,A.; Scheffler,K., Justus Liebigs Annalen der Chemie, 1965, vol. 689, p. 78 - 92
  作者：Rieker,A.、Scheffler,K.

  DOI：——

  日期：——
• 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.
• US4172151A
  申请人：——

  公开号：US4172151A

  公开（公告）日：1979-10-23
• US4219501A
  申请人：——

  公开号：US4219501A

  公开（公告）日：1980-08-26
• US4232043A
  申请人：——

  公开号：US4232043A

  公开（公告）日：1980-11-04