5,7-Diethyltocopherol | 118112-45-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,7-Diethyltocopherol
• 英文别名: 5,7-diethyltocol；5,7-diethyl-2-methyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
• CAS: 118112-45-1
• 化学式: C₃₀H₅₂O₂
• 分子量: 444.742
• InChiKey: GPKLMELPHVJVII-UHFFFAOYSA-N

物化性质

• 沸点：
  530.4±39.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.04
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyl-4-(4-methoxyphenyl)phenoxyl 、 5,7-Diethyltocopherol 以 乙醇 为溶剂， 生成 2,6-di-t-butyl-4-(4-methoxyphenyl)phenol 、 5,7-diethyltocopheroxyl radical
  参考文献：
  名称：

  Synthesis and kinetic study of antioxidant activity of new tocopherol (vitamin E) compounds

  摘要：

  DOI：

  10.1021/jo00264a010
• 作为产物：
  描述：

  Formic acid 5,7-diethyl-2-methyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-yl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 5,7-Diethyltocopherol
  参考文献：
  名称：

  Synthesis and kinetic study of antioxidant activity of new tocopherol (vitamin E) compounds

  摘要：

  DOI：

  10.1021/jo00264a010

文献信息

• Mechanism of prooxidant reaction of vitamin E: kinetic, spectroscopic, and ab initio study of proton-transfer reaction
  作者：Shinichi Nagaoka、Kouhei Sawada、Youji Fukumoto、Umpei Nagashima、Shunji Katsumata、Kazuo Mukai

  DOI：10.1021/j100195a027

  日期：1992.8

  To shed light on the mechanism of proton-transfer reactions, a kinetic, spectroscopic, and ab initio study of the prooxidant action of vitamin E derivatives has been carried out. The second-order rate constants (k(-s)'s) for the reaction of six tocopheroxyl radicals (Toc.'s) with five alkyl hydroperoxides (ROOHs) in benzene were determined spectrophotometrically. The first adiabatic ionization potentials (I(a)'s) of ROOHs were obtained by means of photoelectron spectroscopy. The result indicates that k(-s) increases as the electron-donating capacity of the alkyl substituents of ROOH increases and I(a) decreases. The methylation at the aromatic ring of Toc. reduces the k(-s) for a given ROOH. k(-s) for the reaction of deuterated alkyl hydroperoxides (ROODs) with a Toc. in a mixed solution of benzene and ethanol-d1 was also measured. A deuterium kinetic isotope effect on k(-s) is observed. For a given Toc., plots of log k(-s) vs I(a) for various ROOHs and log k(-s) vs Tafts sigma* constant of alkyl substituents of ROOH are found to be linear. The slope of the plot of log k(-s) vs sigma* for ROOD is similar to that for ROOH. The geometries of ROOHs were optimized, and the Koopmans' theorem first ionization potentials (I(K)'s) for those geometries were calculated with the ab initio method. A plot of log k(-s)the reactions of a Toc. with various ROOHs vs I(K) of the ROOH is also found to be linear. From these results, it is considered that both charge transfer and proton tunneling play important roles in the prooxidant reaction of TocH. The transition state in the prooxidant reaction has properties 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 transfer reactions.
• MUKAI, KAZUO;KAGEYAMA, YUKIO;ISHIDA, TAMIE;FUKUDA, KAZUYUKI, J. ORG. CHEM., 54,(1989) N, C. 552-556
  作者：MUKAI, KAZUO、KAGEYAMA, YUKIO、ISHIDA, TAMIE、FUKUDA, KAZUYUKI

  DOI：——

  日期：——