| 14306-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 14306-91-3
• 化学式: C₂₉H₄₃O₂
• 分子量: 423.659
• InChiKey: GNLMZUYYLVJGPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  21.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  生成 抗氧剂 702 、 2,6-二叔丁基-4-(3,5-二叔丁基-4-羟基苯亚甲基)-2,5-环己二烯-1-酮
  参考文献：
  名称：

  ESR spectra and kinetics of the disproportionation of substituted phenoxy radicals Coomunication 2. Radicals of 2,4,6-trialkyl-substituted mono-, p-bis-, p-tris-, and p-tetraphenols

  摘要：

  DOI：

  10.1007/bf00953918
• 作为产物：
  描述：

  抗氧剂 702 在 苯乙烯 、 air 、 偶氮二异庚腈 作用下， 以 氯苯 为溶剂， 生成
  参考文献：
  名称：

  Antioxidant Activity of o-Bisphenols:  the Role of Intramolecular Hydrogen Bonding

  摘要：

  A kinetic and thermodynamic investigation on the antioxidant activity of 2,2'-methylenebis(6-tertbutyl-4-methylphenol) (2), 2,2'-ethylidenebis(4,6-di-tert-butylphenol) (3), and 4,4'-methylenebis(2,6di-tert-butylphenol) (4) are reported. EPR studies of the equilibration between 3 or 4 and a reference phenol, and the corresponding phenoxyl radicals, allowed us to determine the O-H bond dissociation enthalpy (BDE) of the O-H bond as 81.2 and 81.1 kcal/mol in 3 and 4, respectively. Despite this similarity, the absolute rate constants for the reaction with peroxyl radicals, determined by autoxidation studies under controlled conditions, indicate that the o-bisphenols 2 and 3 behave as excellent antioxidants while the p-bisphenol 4 is less effective by a factor of 64 and 22, respectively. FT-IR spectroscopy and product studies suggest that the very good antioxidant activity of the o-bisphenols largely arises from both the reduced steric crowding about the hydroxyl group and the stabilization of the aroxyl radical due to the formation of an intramolecular hydrogen bond between the residual OH and the oxygen radical center.

  DOI：

  10.1021/jo0342931

文献信息

• ESR spectra and kinetics of the disproportionation of substituted phenoxy radicals Coomunication 2. Radicals of 2,4,6-trialkyl-substituted mono-, p-bis-, p-tris-, and p-tetraphenols
  作者：V. A. Roginskii

  DOI：10.1007/bf00953918

  日期：1985.9
• Antioxidant Activity of <i>o</i>-Bisphenols:  the Role of Intramolecular Hydrogen Bonding
  作者：Riccardo Amorati、Marco Lucarini、Veronica Mugnaini、Gian Franco Pedulli

  DOI：10.1021/jo0342931

  日期：2003.6.1

  A kinetic and thermodynamic investigation on the antioxidant activity of 2,2'-methylenebis(6-tertbutyl-4-methylphenol) (2), 2,2'-ethylidenebis(4,6-di-tert-butylphenol) (3), and 4,4'-methylenebis(2,6di-tert-butylphenol) (4) are reported. EPR studies of the equilibration between 3 or 4 and a reference phenol, and the corresponding phenoxyl radicals, allowed us to determine the O-H bond dissociation enthalpy (BDE) of the O-H bond as 81.2 and 81.1 kcal/mol in 3 and 4, respectively. Despite this similarity, the absolute rate constants for the reaction with peroxyl radicals, determined by autoxidation studies under controlled conditions, indicate that the o-bisphenols 2 and 3 behave as excellent antioxidants while the p-bisphenol 4 is less effective by a factor of 64 and 22, respectively. FT-IR spectroscopy and product studies suggest that the very good antioxidant activity of the o-bisphenols largely arises from both the reduced steric crowding about the hydroxyl group and the stabilization of the aroxyl radical due to the formation of an intramolecular hydrogen bond between the residual OH and the oxygen radical center.