3,5-di-tert-butylcatechol radical | 85693-00-1

• 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: 3,5-di-tert-butylcatechol radical
• CAS: 85693-00-1
• 化学式: C₁₄H₂₁O₂
• 分子量: 221.32
• InChiKey: PJMLOPWPIFLAKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  3,5-di-tert-butylcatechol radical 生成 3,5-二叔丁基邻苯二酚 、 3,5-二叔丁基邻苯醌
  参考文献：
  名称：

  Study of disproportionation of some substituted 2-Hydroxyphenoxyl radicals

  摘要：

  DOI：

  10.1007/bf00957923
• 作为产物：
  描述：

  3,5-二叔丁基邻苯二酚 在 1,1-二苯-2-苦基肼 作用下， 以 正己烷 为溶剂， 生成 3,5-di-tert-butylcatechol radical
  参考文献：
  名称：

  Media Effects on Antioxidant Activities of Phenols and Catechols

  摘要：

  The H-atom donating activities of 2,6-di-tert-butyl-4-methylphenol (BHT), 2,6-di-tert-butyl-4-methoxyphenol (DBHA), 2,2,5,7,8-pentamethyl-6-hydroxychroman (PMHC), and 3,5-di-tert-butylcatechol (DTBC) toward the nitrogen-centered 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were measured by stopped flow methods in hexane, 1-propanol, tert-butyl alcohol, and acetone. Decreases in these activities on transferring: from hexane to the hydrogen bond accepting (HBA) solvents, the kinetic solvent effect (KSE), are attributed to hydrogen bonding from the phenolic group. Steric hindrance accounts for a lower decrease observed for the highly hindered BHT and DBHA compared to PMHC. The catechol, DTBC, a very active H-atom donor to DPPH in hexane; showed a dramatic loss of activity in HBA solvents, especially acetone. Higher H-atom donating activities of BHT, DBHA, and PMHC were observed toward the oxygen-centered radical of 2,6-di-tert-butyl-4-(4'-methoxyphenyl)phenoxyl and the decreases in activity in the HBA solvents paralleled those found with DPPH; Thus the KSE was found to be independent of the nature of the abstracting radical for DPPH and DBMP. The inhibition of the oxygen uptake (IOU) method was used to determine the antioxidant activities (k(inh)) of alpha-tocopherol, PMHC, catechol, and DTBC during free radical autoxidation of styrene and mixtures of styrene and tert-butyl alcohol. The k(inh) of alpha-tocopherol and PMHC dropped to one-tenth of the values with increasing tert-butyl alcohol content due to the HBA activity of the alcohol compared to styrene.

  DOI：

  10.1021/ja990878u

文献信息

• Study of disproportionation of some substituted 2-Hydroxyphenoxyl radicals
  作者：B. L. Tumanskii、A. I. Prokof'ev、N. N. Bubnov、S. P. Solodovnikov、A. A. Khodak

  DOI：10.1007/bf00957923

  日期：1983.2
• Media Effects on Antioxidant Activities of Phenols and Catechols
  作者：L. R. C. Barclay、C. E. Edwards、M. R. Vinqvist

  DOI：10.1021/ja990878u

  日期：1999.7.1

  The H-atom donating activities of 2,6-di-tert-butyl-4-methylphenol (BHT), 2,6-di-tert-butyl-4-methoxyphenol (DBHA), 2,2,5,7,8-pentamethyl-6-hydroxychroman (PMHC), and 3,5-di-tert-butylcatechol (DTBC) toward the nitrogen-centered 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were measured by stopped flow methods in hexane, 1-propanol, tert-butyl alcohol, and acetone. Decreases in these activities on transferring: from hexane to the hydrogen bond accepting (HBA) solvents, the kinetic solvent effect (KSE), are attributed to hydrogen bonding from the phenolic group. Steric hindrance accounts for a lower decrease observed for the highly hindered BHT and DBHA compared to PMHC. The catechol, DTBC, a very active H-atom donor to DPPH in hexane; showed a dramatic loss of activity in HBA solvents, especially acetone. Higher H-atom donating activities of BHT, DBHA, and PMHC were observed toward the oxygen-centered radical of 2,6-di-tert-butyl-4-(4'-methoxyphenyl)phenoxyl and the decreases in activity in the HBA solvents paralleled those found with DPPH; Thus the KSE was found to be independent of the nature of the abstracting radical for DPPH and DBMP. The inhibition of the oxygen uptake (IOU) method was used to determine the antioxidant activities (k(inh)) of alpha-tocopherol, PMHC, catechol, and DTBC during free radical autoxidation of styrene and mixtures of styrene and tert-butyl alcohol. The k(inh) of alpha-tocopherol and PMHC dropped to one-tenth of the values with increasing tert-butyl alcohol content due to the HBA activity of the alcohol compared to styrene.