2-(perfluoroisopropyl)hydroquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(perfluoroisopropyl)hydroquinone
• 英文别名: 2-(perfluoropropan-2-yl)benzene-1,4-diol；2-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)benzene-1,4-diol；2-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)benzene-1,4-diol
• 化学式: C₉H₅F₇O₂
• 分子量: 278.126
• InChiKey: FJDPHDFREOLZEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-hydroxy-4-perfluoroisopropyl-2,5-cyclohexadien-1-one 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.2h， 以76%的产率得到2-(perfluoroisopropyl)hydroquinone
  参考文献：
  名称：

  Perfluoroalkyl migration in the rearrangement of 4-perfluoroalkyl-4-quinols

  摘要：

  Heating a DMSO solution of 4-(perfluoro-n-alkyl)-4-hydroxy-2,5-cyclohexadien-1-one (4-perfluoroalkyl-4-quinols) in the presence of a catalytic amount of base brought about 1,2-migration of the perfluoroalkyl group to give 2-(perfluoro-n-alkyl)hydroquinone or 5-(perfluoro-n-alkyl)-2-cyclohexene-1,4-dione depending upon the substitution pattern of the quinol. The similar rearrangement of 4-perfluoroisopropyl-4-hydroxy-2,5-cyclohexadien-1-one occurred very smoothly at room temperature under the basic conditions. 5-Hydroxy-4-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one underwent the base-induced rearrangement to afford a perfluorooctylated succinimide derivative. On the other hand, 5-hydroxy-3-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one and 5-hydroxy-1-isobutyl-5-perfluorooctyl-3-pyrrolin-2-one did not suffer any rearrangement, although their structures were very similar to the 4-methylated one.

  DOI：

  10.1016/s0040-4020(01)86584-4

文献信息

• Perfluoroalkyl migration in the rearrangement of 4-perfluoroalkyl-4-quinols
  作者：Hidemitsu Uno、Ayumi Yayama、Hitomi Suzuki

  DOI：10.1016/s0040-4020(01)86584-4

  日期：1992.9

  Heating a DMSO solution of 4-(perfluoro-n-alkyl)-4-hydroxy-2,5-cyclohexadien-1-one (4-perfluoroalkyl-4-quinols) in the presence of a catalytic amount of base brought about 1,2-migration of the perfluoroalkyl group to give 2-(perfluoro-n-alkyl)hydroquinone or 5-(perfluoro-n-alkyl)-2-cyclohexene-1,4-dione depending upon the substitution pattern of the quinol. The similar rearrangement of 4-perfluoroisopropyl-4-hydroxy-2,5-cyclohexadien-1-one occurred very smoothly at room temperature under the basic conditions. 5-Hydroxy-4-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one underwent the base-induced rearrangement to afford a perfluorooctylated succinimide derivative. On the other hand, 5-hydroxy-3-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one and 5-hydroxy-1-isobutyl-5-perfluorooctyl-3-pyrrolin-2-one did not suffer any rearrangement, although their structures were very similar to the 4-methylated one.