3,3,4,6,6,7,7,9,9,10,10,12,12,13,13,15,15,16,16,18,18,18-Docosafluoro-5,8,11,14,17-pentaoxaoctadecane-1,2-diol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 3,3,4,6,6,7,7,9,9,10,10,12,12,13,13,15,15,16,16,18,18,18-Docosafluoro-5,8,11,14,17-pentaoxaoctadecane-1,2-diol
• 英文别名: 3,3,4-Trifluoro-4-[1,1,2,2-tetrafluoro-2-[1,1,2,2-tetrafluoro-2-[1,1,2,2-tetrafluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]ethoxy]ethoxy]butane-1,2-diol
• 化学式: C₁₃H₆F₂₂O₇
• 分子量: 692.151
• InChiKey: BEPAQPDTZBGSPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  2,2-二甲基-1,3-二氧环戊烷 、 Perfluoro-3,6,9,12,15-pentaoxahexadec-1-ene 在 盐酸 、 甲醇 、 水 作用下， 反应 5.0h， 生成 3-(Difluoromethyl)-3,5,5,6,6,8,8,9,9,11,11,12,12,14,14,15,15,17,17,17-eicosafluoro-4,7,10,13,16-pentaoxaheptadecane-1,2-diol 、 3,3,4,6,6,7,7,9,9,10,10,12,12,13,13,15,15,16,16,18,18,18-Docosafluoro-5,8,11,14,17-pentaoxaoctadecane-1,2-diol
  参考文献：
  名称：

  Radical addition reactions of fluorinated species. Part 7. Highly selective two-step synthesis of 1-(polyfluoroalkyl)ethane-1,2-diols; regioselectivity of the additions of methylated 1,3-dioxolanes to perfluoroolefins

  摘要：

  The two-step synthesis of the diols is based on the radical addition of 2,2-dimethyl-1,3-dioxolane (1), a protected ethane-1,2-diol, to perfluoroalk-1-enes R-F-CF=CF2 (RF=CF3, C9F19; 2, 3) and perfluoro[trifluorovinyl (poly)ethers] RFO-CF=CF2 (R-F=C3F7, C3F7O[CF(CF3)CF2], CF3(OCF2CF2)(4); 4-6) with preparative yields above 90% in each step. The additions were initiated photochemically or by dibenzoyl peroxide and were completely chemoselective and almost completely regioselective. 4-Fluoroalkylated dioxolanes obtained (7-11) were deprotected by acid methanolysis to afford 1-polyfluoroalkylethane-1,2-diols (12-16). 1,3-Dioxolane (27) or 2,2,4-trimethyl-1, 3-dioxolane (30) reacted at two centers to yield regioisomeric mixtures of fluoroalkylated dioxolanes. The factors influencing fluoroolefin and dioxolane regioselectivity are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00356-x

文献信息

• Radical addition reactions of fluorinated species. Part 7. Highly selective two-step synthesis of 1-(polyfluoroalkyl)ethane-1,2-diols; regioselectivity of the additions of methylated 1,3-dioxolanes to perfluoroolefins
  作者：Vladimı́r Cı́rkva、Oldrich Paleta

  DOI：10.1016/s0022-1139(98)00356-x

  日期：1999.4

  The two-step synthesis of the diols is based on the radical addition of 2,2-dimethyl-1,3-dioxolane (1), a protected ethane-1,2-diol, to perfluoroalk-1-enes R-F-CF=CF2 (RF=CF3, C9F19; 2, 3) and perfluoro[trifluorovinyl (poly)ethers] RFO-CF=CF2 (R-F=C3F7, C3F7O[CF(CF3)CF2], CF3(OCF2CF2)(4); 4-6) with preparative yields above 90% in each step. The additions were initiated photochemically or by dibenzoyl peroxide and were completely chemoselective and almost completely regioselective. 4-Fluoroalkylated dioxolanes obtained (7-11) were deprotected by acid methanolysis to afford 1-polyfluoroalkylethane-1,2-diols (12-16). 1,3-Dioxolane (27) or 2,2,4-trimethyl-1, 3-dioxolane (30) reacted at two centers to yield regioisomeric mixtures of fluoroalkylated dioxolanes. The factors influencing fluoroolefin and dioxolane regioselectivity are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.