1H,1H,2H,2H-perfluorodecylmagnesium iodide | 249301-95-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1H,1H,2H,2H-perfluorodecylmagnesium iodide
• CAS: 249301-95-9
• 化学式: C₁₀H₄F₁₇IMg
• 分子量: 598.324
• InChiKey: LYBSLPJHWFJMQO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1H,1H,2H,2H-perfluorodecylmagnesium iodide 在 sodium hydroxide 、 三氟甲苯 、 4 A molecular sieve 、 四丁基碘化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 76.0h， 生成 2-(4-chloro-phenyl)-4-[4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-1-methoxy-undecyl]-[1,3]dioxolane
  参考文献：
  名称：

  氟乙二醇衍生物：新型羰基保护基

  摘要：

  制备了氟乙二醇衍生物5，并作为氟合成中用于保护羰基的试剂进行了评估。由氟二醇5b（Rf ＝n- C 8 F 17）与羰基化合物形成的缩醛可以通过简单的氟有机萃取来分离和纯化。

  DOI：

  10.1016/j.tet.2004.07.031
• 作为产物：
  描述：

  1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-十七氟-10-碘庚烷 在 magnesium 作用下， 以 乙醚 为溶剂， 生成 1H,1H,2H,2H-perfluorodecylmagnesium iodide
  参考文献：
  名称：

  Fluorinated Analogues of tert-Butyl Alcohol as Novel Protecting Groups for Use in Fluorous Synthesis

  摘要：

  [GRAPHICS]A series of fluorous derivatives of tert-butyl alcohol were prepared and evaluated as reagents for the protection of carboxylic acids for use in fluorous synthesis. Alcohol 3b can be employed efficiently to protect and immobilize medium-size nonpolar carboxylic acids in a fluorous phase.

  DOI：

  10.1021/ol0166505

文献信息

• Synthesis of perfluoroalkyl steroids as CO-emulsifying agents for 1-bromoperfluorooctane and other perfluorocompounds
  作者：C.M. Sharts、A.A. Malik、J.C. Easdon、L.A. Khawli、D.M. Long、D.F. Shellhamer、V.L. Burton、M.K. Porter、L.F. Sprague

  DOI：10.1016/s0022-1139(00)85180-5

  日期：1987.1

  substituted with perfluoroalkyl groups at C-3, C-7, and C-20 positions on the steroid nucleus are described. Synthetic methods employed included coupling of perfluoroalkylcopper with allylic bromides and Grignard reactions. Free radical additions of perfluoroalkyl iodide to unsaturated steroids and reaction of perfluoroalkyl Grignard reagents with 6-ketosteroid were unsuccessful. Perfluoroalkyl -substituted

  描述了在类固醇核的C-3，C-7和C-20位置被全氟烷基取代的类固醇的合成。所使用的合成方法包括全氟烷基铜与烯丙基溴的偶联和格氏反应。全氟烷基碘向不饱和类固醇的自由基加成以及全氟烷基格氏试剂与6-酮类固醇的反应均未成功。需要全氟烷基取代的类固醇作为全乳化全氟辛烷/水乳液中的助乳化剂进行测试，该乳液用作血液替代品（合成血液）。还报道了选择全氟辛基溴化物作为氟碳基血液替代品中的携氧剂以及使用全氟烷基取代的类固醇作为共乳化剂的基本原理。
• Synthesis, properties, and reactions of enantiomerically pure, chiral fluorous phosphines of the formula (menthyl)P(CH2CH2(CF2)n−1CF3)2 (n=6, 8)
  作者：Alain Klose、J.A Gladysz

  DOI：10.1016/s0957-4166(99)00272-4

  日期：1999.7

  Reactions of (menthyl)PH2 and H2C=CHRf6 (menthyl=1R,3R,4S; R-fn=(CF2)(n-1)CF3) or H2C=CHRf8 (AIBN, refluxing THF) give (menthyl)PH(CH2CH2Rfn) and then (menthyl)P(CH2CH2Rfn)(2) (n=6, 7; n=8, 8), but with purification or other difficulties at each stage. Reactions of (menthyl)PCl2 with IMgCH2CH2Rfn give, under careful conditions, analytically pure 7 or 8 in 28-32% yields after distillation. Some R-fn(CH2)(4)R-fn also form. These represent the first chiral (and non-racemic) fluorous phosphines. Reactions of 7 or 8 with [Ir(COD)Cl](2) and CO give trans-[(menthyl)P(CH2CH2Rfn)(2)]Ir(CI)(CO) (n=6, 71%; 8, 51%) as analytically pure yellow oils. Their IR vco values show the donor/acceptor properties of 7 and 8 to be intermediate between those of P((CH2)(3)R-f8)(3) and P((CH2)(4)R-f8)(3) The CF3C6F11 :toluene partition coefficients of 7 and 8 (27 degrees C, 78.4:21.6 and 93.7:6.3) are distinctly lower than those of P((CH2)(2)R-fn)(3) (n=6, 98.8:1.2; n=8, >99.7:<0.3), reflecting the replacement of a linear Cs-8-C-10 group that is ca. 75-80% fluorinated by a cyclic C-10 terpenyl group. Reactions of 7 or 8 with [Rh(COD)Cl](2) give [(menthyl)P(CH2CH2Rfn)(2)]Rh(Cl)(COD) (n=6, 69%; 8, 70%) as orange crystallizable oils. (C) 1999 Elsevier Science Ltd. All rights reserved.