1H,1H,2H,3H,3H-perfluoro-2-iodo-n-tridecan-1-ol | 38550-46-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1H,1H,2H,3H,3H-perfluoro-2-iodo-n-tridecan-1-ol
• 英文别名: 2-iodo-3-(perfluorodecyl)propan-1-ol；1-Tridecanol, 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heneicosafluoro-2-iodo-；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluoro-2-iodotridecan-1-ol
• CAS: 38550-46-8
• 化学式: C₁₃H₆F₂₁IO
• 分子量: 704.061
• InChiKey: QUGHSSKHWRLWSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1H,1H,2H,3H,3H-perfluoro-2-iodo-n-tridecan-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heneicosafluorotridecan-1-ol
  参考文献：
  名称：

  氟代二甲基硫代氨基甲酸酯（F DMTC）的醇保护基

  摘要：

  合成了N，N-双（全氟烷基）硫代氨基甲酰氯（F DMTC-Cls）作为保护醇的试剂。使用结晶的F DMTC- Cl，在室温下在THF中存在氢化钠的情况下，将F DMTC基团以优异的产率引入醇分子中。通过用氟反相硅胶柱进行固相萃取（Fluorous固相萃取； FSPE），将产物与过量的醇分离。所述˚F DMTC组分别容易地通过用氧化除去米氯过苯甲酸（米-CPBA）中，用KHCO随后水解3。

  DOI：

  10.1016/j.tetlet.2006.05.142
• 作为产物：
  描述：

  1-碘全氟癸烷 、 烯丙醇 在 potassium disulphite 、 偶氮二异丁腈 作用下， 以 水 为溶剂， 反应 8.0h， 以94%的产率得到1H,1H,2H,3H,3H-perfluoro-2-iodo-n-tridecan-1-ol
  参考文献：
  名称：

  3-（全氟烷基）丙醇：含氟化学的重要组成部分

  摘要：

  通过将市售的 N-全氟烷基和全氟异烷基碘化物受控自由基加成到烯丙醇中，2-Iodo-3-(全氟烷基)丙醇以优异的产率和数百克的量获得。它们在甲醇中用水合肼和阮内镍催化剂连续还原，以高收率和纯度提供相应的 3-(全氟烷基)丙醇。

  DOI：

  10.1055/s-2007-983779

文献信息

• An Efficient Photoinduced Iodoperfluoroalkylation of Carbon−Carbon Unsaturated Compounds with Perfluoroalkyl Iodides
  作者：Kaname Tsuchii、Motohiro Imura、Nagisa Kamada、Toshikazu Hirao、Akiya Ogawa

  DOI：10.1021/jo0495889

  日期：2004.10.1

  β-perfluoroalkylated vinylic iodides (R−CHC(I)−CH2−RF) in good yields. The photoinitiated reaction of vinylcyclopropanes (c-C3H5−C(R)CH2) with RF-I proceeds via the rearrangement of cyclopropylcarbinyl radical intermediates to the homoallylic radical intermediates, and the corresponding 1,5-iodoperfluoroalkylated products (I−(CH2)2CHC(R)−CH2−RF) are obtained in high yields. Isocyanides (R−NC), as C−N unsaturated

  取决于所用光源的选择，各种不饱和化合物的光诱导碘全氟烷基化通过自由基机理有效地发生。当通过派热克斯（用氙灯照射ħ ν > 300纳米），末端烯烃（R-CH CH 2）和炔（R-C⋮CH）经历与iodoperfluoroalkylation全氟烷基碘（R ˚F -I）区域选择性地，提供R- CH（I）-CH 2 -R ˚F和-R C（I）-R CH ˚F，分别。在末端异位烯的情况下（R-CH C CH 2），光诱导的碘全氟烷基化选择性地发生在末端双键处，从而以良好的收率得到相应的β-全氟烷基化乙烯基碘（R-CH C（I）-CH 2 -R F）。乙烯基环丙烷（c -C 3 H 5 -C（R）CH 2）与R F -I的光引发反应是通过将环丙基羰基自由基中间体和相应的1,5-碘全氟烷基化产物（I -（CH 2）2 CH C（R）-CH 2 -R F）以高收率获得。异氰酸酯（R-NC），作为C-N不
• Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols
  作者：Csongor Szíjjártó、Peter Ivanko、Ferenc T. Takács、Dénes Szabó、József Rábai

  DOI：10.1016/j.jfluchem.2008.01.012

  日期：2008.5

  3-(Perfluoroalkyl)-1-propenes are obtained in excellent yields up to 100-g quantities by deiodination-dehydroxylation reactions of the easily accessible 2-iodo-3-(perfluoroalkyl)-propanols with red phosphorus and catalytic amounts of iodine or with an SnCl2/POCl3 reagent pair in pyridine (fluorous Cornforth reaction). Both methods afford fluorous propenes in high GC purity, the former one has high atom-economy and proceeds safely if the fluorous iodohydrin precursors are added in increments; for the solid ones using a 'hot-melt' dropping funnel. The title fluorous propenes are effectively isolated by co-distillation with pyridine. (c) 2008 Elsevier B.V. All rights reserved.
• Self-assembled monolayers on gold generated from terminally perfluorinated alkanethiols bearing propyl vs. ethyl hydrocarbon spacers
  作者：Oussama Zenasni、Andrew C. Jamison、Maria D. Marquez、T. Randall Lee

  DOI：10.1016/j.jfluchem.2014.09.003

  日期：2014.12

  This paper examines the structural and interfacial properties of terminally perfluorinated self-assembled monolayers (FSAMs) on gold generated from the adsorption of a new series of terminally perfluorinated propanethiols F(CF2)(n)CH2)(3)SH, where n = 8, 10, and 12. Analysis of these FSAMs by ellipsometry and X-ray photoelectron spectroscopy (XPS) confirmed the formation of the monolayer films. The contact angles of water and n-hexadecane on these FSAMs indicated a high degree of hydrophobicity and oleophobicity. Polarization modulation infrared reflection-adsorption spectroscopy (PM-IRRAS) analysis of the films revealed that the fluorinated chains are oriented largely perpendicular to the gold surface. In addition, the FSAMs formed from the new adsorbates were compared to known FSAMs derived from F(CF2)(n)(CH2)(2)SH, where n = 8, 10, and 12, to examine the influence of the number of CH2 groups in the short alkyl spacer upon the conformational order and packing structure of the films. Analysis of the XPS spectra for the normalized peak intensity of the F 1s and S 2p binding energies for both types of films suggest a slight increase in packing density for the chains having the propyl vs. the ethyl hydrocarbon spacer. This conclusion is consistent with the observed decrease in the wetting behavior of hexadecane on the FSAMs formed from the new adsorbates. However, the preponderance of the data indicates that these two series of partially fluorinated alkanethiols form films with highly similar structure/packing characteristics with no discernible "odd-even" effect between the two series. (C) 2014 Elsevier B.V. All rights reserved.
• 10.1071/jo062606x
  作者：Stuart, Alison M.、Vidal, Jose A.

  DOI：10.1071/jo062606x

  日期：——
• Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols
  作者：Masaru Kojima、Yutaka Nakamura、Takuma Ishikawa、Seiji Takeuchi

  DOI：10.1016/j.tetlet.2006.05.142

  日期：2006.8

  N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase

  合成了N，N-双（全氟烷基）硫代氨基甲酰氯（F DMTC-Cls）作为保护醇的试剂。使用结晶的F DMTC- Cl，在室温下在THF中存在氢化钠的情况下，将F DMTC基团以优异的产率引入醇分子中。通过用氟反相硅胶柱进行固相萃取（Fluorous固相萃取； FSPE），将产物与过量的醇分离。所述˚F DMTC组分别容易地通过用氧化除去米氯过苯甲酸（米-CPBA）中，用KHCO随后水解3。