4-hydroxy-4-perfluoroisopropyl-2,5-cyclohexadien-1-one | 135325-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-4-perfluoroisopropyl-2,5-cyclohexadien-1-one
• 英文别名: 4-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-4-hydroxycyclohexa-2,5-dien-1-one
• CAS: 135325-19-8
• 化学式: C₉H₅F₇O₂
• 分子量: 278.126
• InChiKey: QYTMRTWALGTRNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  七氟-2-碘代丙烷 、 对苯醌 在 甲基锂 、 lithium bromide 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以19%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

• Acetic acid derivatives and their production
  申请人：ETHYL CORPORATION

  公开号：EP0426333A2

  公开（公告）日：1991-05-08

  Compounds of the formula where n is an integer from 1 to 12, R and R₁ are the same or different and are hydrogen or C₁ to C₆ linear or branched alkyl as well as their physiologically active salts and amides thereof and the enantiomers, mixtures and racemates are disclosed. Intermediates useful in preparing the above compounds are also disclosed as are processes for preparing these compounds.

  式中的化合物 其中 n 为 1 至 12 的整数，R 和 R₁ 相同或不同，且为氢或 C₁ 至 C₆ 直链或支链烷基，公开了它们的生理活性盐和酰胺及其对映体、混合物和外消旋体。此外，还公开了用于制备上述化合物的中间体以及制备这些化合物的工艺。
• US5302752A
  申请人：——

  公开号：US5302752A

  公开（公告）日：1994-04-12