3,5-di-tert-butyl-4-hydroxybenzyl 2,4-dimethylphenyl ether | 131544-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-di-tert-butyl-4-hydroxybenzyl 2,4-dimethylphenyl ether
• 英文别名: 2,6-Ditert-butyl-4-[(2,4-dimethylphenoxy)methyl]phenol
• CAS: 131544-12-2
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: PJOIOMXUAGGUKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one 、 2,4-二甲基苯酚 、 三乙胺 以17%的产率得到
  参考文献：
  名称：

  OMURA, KENJI, J. ORG. CHEM., 56,(1991) N, C. 921-926

  摘要：

  DOI：

文献信息

• The reaction of the 2,6-di-tert-butyl-4-methylphenoxy radical with phenols
  作者：Kanji Omura

  DOI：10.1021/jo00003a006

  日期：1991.2

  Dimer 3 dissociates in solution to give the phenoxy radical 4. When solid 3 is dissolved in a solution of phenol 11a, radical 4 dehydrogenates the phenol to afford phenol 5 and phenoxy radical 12. Radical 12 couples with more 4 to afford principally bis(cyclohexadienone) 16a and a minor amount of the dimeric bis(cyclohexadienone) 13. The preferential formation of 16a over 13 is explained as the result of a solvent-cage reaction. Compounds 13 and 16a are isomerized in the presence of silica gel or triethylamine to 4,4'-dihydroxybiphenyl 14 and phenolic dienone 17a, respectively. Compound 13 is relatively stable in hexane at 30-degrees-C, while 16a slowly dissociates under these conditions to afford parent radicals 4 and 12. If 11a is present, radical 4 either recombines with 12 or dehydrogenates the phenol. Two radicals of 12 generated by the dissociation of 16a and the subsequent dehydrogenation of 11a couple to give 13. Therefore, dissolving 3 in hexane containing excess 11a and keeping the resulting solution at 30-degrees-C results in the preferential formation of 13. Dissolving 3 in triethylamine containing phenols 11 or 21 similarly affords dienones 17 or 23. The yields of these dienones increase with increasing electron-donating capability of the substituent on the phenol ring.