4-hydroxy-2,3,5,6-tetramethyl-4-perfluorooctyl-2,5-hexadien-1-one | 135957-83-4

• 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-hydroxy-2,3,5,6-tetramethyl-4-perfluorooctyl-2,5-hexadien-1-one
• 英文别名: 4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)-4-hydroxy-2,3,5,6-tetramethylcyclohexa-2,5-dien-1-one
• CAS: 135957-83-4
• 化学式: C₁₈H₁₃F₁₇O₂
• 分子量: 584.273
• InChiKey: JYKNTQMJMDAIER-UHFFFAOYSA-N

物化性质

• 沸点：
  358.5±42.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2,3,5,6-tetramethyl-4-perfluorooctyl-2,5-hexadien-1-one 反应 2160.0h， 生成 2,3,4,5-tetramethyl-4-perfluorononanoyl-2-cyclopenten-1-one
  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
• 作为产物：
  描述：

  全氟辛基碘烷 、 杜醌 在 甲基锂 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到4-hydroxy-2,3,5,6-tetramethyl-4-perfluorooctyl-2,5-hexadien-1-one
  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

• Uno, Hidemitsu; Yayama, Ayumi; Suzuki, Hitomi, Chemistry Letters, 1991, # 7, p. 1165 - 1168
  作者：Uno, Hidemitsu、Yayama, Ayumi、Suzuki, Hitomi

  DOI：——

  日期：——