4-acetoxy-2,6-di-tert-butylcyclohexa-2,5-dienone | 1005452-59-4

• 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: 4-acetoxy-2,6-di-tert-butylcyclohexa-2,5-dienone
• CAS: 1005452-59-4
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: XXORBYVVNPXNDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.3±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-bromo-2,6-di-tert-butyl-2,5-cyclohexadienone 、 溶剂黄146 在 sodium acetate 、 silver perchlorate 作用下， 反应 0.07h， 以64%的产率得到3,5-二叔丁基-4-羟基苄基乙酸酯
  参考文献：
  名称：

  Electron Transfer between Protonated and Unprotonated Phenoxyl Radicals¹

  摘要：

  [GRAPHICS]The reaction of phenoxyl radicals with acids is investigated. 2,4,6-Tri-tert-butylphenoxyl radical (13), a persistent radical, deteriorates in MeOH/PhH in the presence of an acid yielding 4-methoxycyclohexa-2,5-dienone 18a and the parent phenol (14). The reaction is facilitated by a strong acid. Treatment of 2,6-di-tert-butyl-4-methylphenoxyl radical (2), a short-lived radical, generated by dissociation of its dimer, with an acid in MeOH provides 4-methoxycyclohexa-2,5-dienone 4 and the products from disproportionation of 2 including the parent phenol (3). A strong acid in a high concentration favors the formation of 4 while the yield of 3 is always kept high. Oxidation of the parent phenol (33) with PbO2 to generate transient 2,6-di-tert-butylphenoxyl radical (35) in AcOH/H2O containing an added acid provides eventually p-benzoquinone 39 and 4,4'-diphenoquinone 42, the product from dimerization of 35. A strong acid in a high concentration favors the formation of 39. These results suggest that a phenoxyl radical is protonated by an acid and electron transfer takes place from another phenoxyl radical to the protonated phenoxyl radical, thus generating the phenoxyl cation, which can add an oxygen nucleophile, and the phenol (eq 5). The electron transfer is a fast reaction.

  DOI：

  10.1021/jo701948a