(1-((4R,5R)-2,2-dimethyl-5-(1-hydroxy-1,1-bis(perfluorooctyl)methyl-1,3-dioxolan-4-yl)perfluorononan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-((4R,5R)-2,2-dimethyl-5-(1-hydroxy-1,1-bis(perfluorooctyl)methyl-1,3-dioxolan-4-yl)perfluorononan-1-one
• 英文别名: 1-((4R,5R)-2,2-dimethyl-5-(1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,17-tetratriacontafluoro-9-hydroxyheptadecan-9-yl)-1,3-dioxolan-4-yl)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononan-1-one；1-[(4R,5R)-2,2-dimethyl-5-(1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,17-tetratriacontafluoro-9-hydroxyheptadecan-9-yl)-1,3-dioxolan-4-yl]-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononan-1-one
• 化学式: C₃₁H₉F₅₁O₄
• 分子量: 1414.33
• InChiKey: SLXSWBHDNWYKSY-WVZVXSGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  86
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  55

反应信息

• 作为反应物：
  描述：

  (1-((4R,5R)-2,2-dimethyl-5-(1-hydroxy-1,1-bis(perfluorooctyl)methyl-1,3-dioxolan-4-yl)perfluorononan-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 以73%的产率得到((α'S,4R,5S)-2,2-dimethyl-α,α,α'-tris(perfluorooctyl)-1,3-dioxolane-4,5-dimethanol
  参考文献：
  名称：

  Synthesis of a Fluorous Ligand and Its Application for Asymmetric Addition of Dimethylzinc to Aldehydes

  摘要：

  A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.

  DOI：

  10.1021/ol070466n
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 、 全氟辛基碘烷 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 以71%的产率得到(1-((4R,5R)-2,2-dimethyl-5-(1-hydroxy-1,1-bis(perfluorooctyl)methyl-1,3-dioxolan-4-yl)perfluorononan-1-one
  参考文献：
  名称：

  Synthesis of a Fluorous Ligand and Its Application for Asymmetric Addition of Dimethylzinc to Aldehydes

  摘要：

  A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.

  DOI：

  10.1021/ol070466n