2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-11-iodo-11-trimethylsilanyl-undecanoic acid methyl ester | 291545-34-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-11-iodo-11-trimethylsilanyl-undecanoic acid methyl ester
• CAS: 291545-34-1
• 化学式: C₁₅H₁₅F₁₆IO₂Si
• 分子量: 686.247
• InChiKey: KRPILIAPASQEMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-11-iodo-11-trimethylsilanyl-undecanoic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 以90%的产率得到2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-11-iodo-11-trimethylsilanyl-undecan-1-ol
  参考文献：
  名称：

  Application of Trimethylvinylsilane as a Convenient Synthetic Precursor of (Perfluoroalkyl)ethenes:  An Unusual Fluoride-Induced Elimination−Desilylation Coupled Reaction

  摘要：

  [GRAPHICS]A convenient and effective method for the preparation of perfluoroalkylated ethenes is described. First, the free radical addition of perfluoroalkyl iodides to trimethylvinylsllane in the presence of AlBN gave iodoethylsilane intermediates (F(CF(2))(n)CH(2)CHISiMe(3), n = 4 (1), 6 (2), 8 (3), 10 (4); 94-99%). Then an unusual dehydrohalogenation-desilylation reaction was effected by tetrabutylammonium fluoride, and finally the product isolation (F(CF(2))(n)CH=CH(2) (5-8), 62-87%) was facilitated using a fluorous phase separation technique. This novel approach can also be applied to adjust short C(2) hydrocarbon units to functionalized fluorinated segments (e.g., HOCH(2)(CF(2))(8)CH=CH(2) (11), 71%), All structures were verified by state-of-the-art multinuclear one- and two-dimensional NMR experiments involving both homo- ((19)F-(19)F) and heteronuclear ((1)H-(13)C, (19)F-(13)C) correlations based on the GMQFCOPS and inverse (1)H and/or (19)F detected GHSQC, GHMQC sequences with broad-band adiabatic (13)C decoupling.

  DOI：

  10.1021/ol006105o
• 作为产物：
  描述：

  methyl 9-iodoperfluorononanoate 、 乙烯基三甲基硅烷 在 偶氮二异丁腈 作用下， 反应 8.0h， 以98%的产率得到2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-11-iodo-11-trimethylsilanyl-undecanoic acid methyl ester
  参考文献：
  名称：

  Application of Trimethylvinylsilane as a Convenient Synthetic Precursor of (Perfluoroalkyl)ethenes:  An Unusual Fluoride-Induced Elimination−Desilylation Coupled Reaction

  摘要：

  [GRAPHICS]A convenient and effective method for the preparation of perfluoroalkylated ethenes is described. First, the free radical addition of perfluoroalkyl iodides to trimethylvinylsllane in the presence of AlBN gave iodoethylsilane intermediates (F(CF(2))(n)CH(2)CHISiMe(3), n = 4 (1), 6 (2), 8 (3), 10 (4); 94-99%). Then an unusual dehydrohalogenation-desilylation reaction was effected by tetrabutylammonium fluoride, and finally the product isolation (F(CF(2))(n)CH=CH(2) (5-8), 62-87%) was facilitated using a fluorous phase separation technique. This novel approach can also be applied to adjust short C(2) hydrocarbon units to functionalized fluorinated segments (e.g., HOCH(2)(CF(2))(8)CH=CH(2) (11), 71%), All structures were verified by state-of-the-art multinuclear one- and two-dimensional NMR experiments involving both homo- ((19)F-(19)F) and heteronuclear ((1)H-(13)C, (19)F-(13)C) correlations based on the GMQFCOPS and inverse (1)H and/or (19)F detected GHSQC, GHMQC sequences with broad-band adiabatic (13)C decoupling.

  DOI：

  10.1021/ol006105o