4-Hydroxyphenyl 4-(tetradecyloxy)phenyl telluride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Hydroxyphenyl 4-(tetradecyloxy)phenyl telluride
• 英文别名: 4-(4-Tetradecoxyphenyl)tellanylphenol
• 化学式: C₂₆H₃₈O₂Te
• 分子量: 510.187
• InChiKey: OFUNBWFRKCOCFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴代十四烷 、 bis(4-hydroxyphenyl)telluride 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以36%的产率得到4-Hydroxyphenyl 4-(tetradecyloxy)phenyl telluride
  参考文献：
  名称：

  Catalytic Antioxidant Activity of Diaryl Tellurides in a Two-Phase Lipid Peroxidation Model

  摘要：

  Diaryl tellurides, diaryl sulfides, ebselen, probucol, BHT, trolox, and vitamin E were assessed for their capacity to inhibit ate-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system containing N-acetylcysteine as a thiol reducing agent in the aqueous phase. The progress of peroxidation in the organic layer was monitored by HPLC with UV detection, and the inhibited rate of peroxidation, R(inh), and the duration of the inhibited phase, T-inh, were determined. In catalytic amounts (40 mu M), both phenolic and nonphenolic diaryl tellurides efficiently inhibited peroxidation in the chlorobenzene layer until the thiol reducing agent in the aqueous phase had been completely oxidized to the corresponding disulfide. Although efficient, trolox and vitamin E offered antioxidant protection only on a stoichiometric basis. BHT, probucol, and ebselen all showed poor antioxidant capacity under the conditions used. Some phenolic diaryl sulfides were moderately efficient inhibitors, with the antioxidant protection enduring for a considerable time without consumption of N-acetylcysteine in the aqueous phase. It is proposed that the diaryl tellurides act as hydrogen atom and/or electron donors toward peroxyl radicals. Further oxidation/hydrolysis probably provides tellurium(IV) dihydroxides, which can recycle to the active antioxidant through reduction by N-acetylcysteine at the water/chlorobenzene interphase.

  DOI：

  10.1021/jo00119a024

文献信息

• Catalytic Antioxidant Activity of Diaryl Tellurides in a Two-Phase Lipid Peroxidation Model
  作者：Kerstin Vessman、Mikael Ekstroem、Mats Berglund、Carl-Magnus Andersson、Lars Engman

  DOI：10.1021/jo00119a024

  日期：1995.7

  Diaryl tellurides, diaryl sulfides, ebselen, probucol, BHT, trolox, and vitamin E were assessed for their capacity to inhibit ate-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system containing N-acetylcysteine as a thiol reducing agent in the aqueous phase. The progress of peroxidation in the organic layer was monitored by HPLC with UV detection, and the inhibited rate of peroxidation, R(inh), and the duration of the inhibited phase, T-inh, were determined. In catalytic amounts (40 mu M), both phenolic and nonphenolic diaryl tellurides efficiently inhibited peroxidation in the chlorobenzene layer until the thiol reducing agent in the aqueous phase had been completely oxidized to the corresponding disulfide. Although efficient, trolox and vitamin E offered antioxidant protection only on a stoichiometric basis. BHT, probucol, and ebselen all showed poor antioxidant capacity under the conditions used. Some phenolic diaryl sulfides were moderately efficient inhibitors, with the antioxidant protection enduring for a considerable time without consumption of N-acetylcysteine in the aqueous phase. It is proposed that the diaryl tellurides act as hydrogen atom and/or electron donors toward peroxyl radicals. Further oxidation/hydrolysis probably provides tellurium(IV) dihydroxides, which can recycle to the active antioxidant through reduction by N-acetylcysteine at the water/chlorobenzene interphase.