(R*,S*)-7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-1,4,4a,9a-tetrahydroxanthene-1,4-dione | 66487-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R*,S*)-7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-1,4,4a,9a-tetrahydroxanthene-1,4-dione
• 英文别名: 7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-9,9a-dihydro-4aH-xanthene-1,4-dione；7-Hydroxy-2,3,4a,5,6,8,9a-heptamethyl-1,4-dioxo-1,4-dihydro-xanthen；Didurochinon；9H-Xanthene-1,4(4ah,9ah)-dione, 7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-；7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-9H-xanthene-1,4-dione
• CAS: 66487-37-4
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: PHKZIPGAUZGGSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  杜醌 在 potassium tert-butylate 、 甲基锂 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (R*,S*)-7-hydroxy-2,3,4a,5,6,8,9a-heptamethyl-1,4,4a,9a-tetrahydroxanthene-1,4-dione
  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.