4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heneicosafluorotridecan-1-ol | 181655-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heneicosafluorotridecan-1-ol
• 英文别名: 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluorotridecane-1-ol；1H,1H,2H,2H,3H,3H-perfluorotridecan-1-ol；3-(perfluorodecyl)propan-1-ol；3-(perfluorodecyl)propanol；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-henicosafluorotridecan-1-ol
• CAS: 181655-66-3
• 化学式: C₁₃H₇F₂₁O
• 分子量: 578.164
• InChiKey: SCBNDEVVOYETPP-UHFFFAOYSA-N

物化性质

• 熔点：
  86-89 °C
• 沸点：
  110 °C(Press: 0.1 Torr)
• 密度：
  1.626±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 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：

  4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heneicosafluorotridecan-1-ol 在 磷酸 、 phosphorus pentoxide 、 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (4S)-2-[1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,18,18,19,19,20,20,21,21,22,22,23,23,24,24,25,25,26,26,27,27,27-dotetracontafluoro-14-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]heptacosan-14-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  对映纯氟双（恶唑啉）：合成及其在催化不对称反应中的应用

  摘要：

  已经通过简单的反应序列合成了各种氟含量为52.7至58.7％的对映纯氟双（恶唑啉），该反应涉及通过将相应的非氟双（恶唑啉）烷基化而引入两个氟化马尾辫。这些新的配体已被钯催化的碳-亲核试剂对rac-（E）-1,3-二苯基丙烯基乙酸乙烯酯进行钯催化的烷基化反应，以及在铜催化的环烯烃的氧化反应中使用了这些新的配体。这些配体分别显示出高达98％和77％的对映选择性，非常接近于使用类似的非氟双（恶唑啉）获得的对映选择性。这些配体可以通过液-液萃取或固-液分离轻松回收，并以相同的对映选择性重复使用。

  DOI：

  10.1021/jo049853q
• 作为产物：
  描述：

  1-碘全氟癸烷 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 作用下， 以 四氢呋喃 为溶剂， 生成 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

文献信息

• 3-(Perfluoroalkyl)propanols: Valuable Building Blocks for Fluorous Chemistry
  作者：József Rábai、Csongor Szíjjártó、Peter Ivanko、Dénes Szabó

  DOI：10.1055/s-2007-983779

  日期：2007.8

  2-Iodo-3-(perfluoroalkyl)propanols are obtained in excellent yields and several-hundred-gram quantities by the controlled radical addition of commercially available N-perfluoroalkyl and perfluoroisoalkyl iodides to allyl alcohol. Their consecutive reduction with hydrazine hydrate and Raney nickel catalyst in methanol afforded the corresponding 3-(perfluoroalkyl)propanols in high yields and purity.

  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。
• Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates
  作者：Bálint Menczinger、Anikó Nemes、Csongor Szíjjártó、József Rábai

  DOI：10.1016/j.jfluchem.2018.02.014

  日期：2018.6

  Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [(CnF2n+1(CH2)mSH); m/n = 3/4,6,8,10, 4a-d; m/n = 2/6, 8; m/n = 1/1,2,3,7,8H, 12a-e] was developed starting from commercially available fluorous alcohols (1a-d, 5, 9a-e). The intermediate (perfluoroalkyl)alkyl iodides and/or sulfonates were reacted with potassium thioacetate in DMF, and the resulting thioacetates were deacetylated by

  （全氟烷基）烷硫醇[（C n F 2n + 1（CH 2）m SH）; 米/ Ñ  = 3 / 4,6,8,10，4A - d ; m / n  = 2/ 6，8 ; M / N  = 1 / 1,2,3,7,8H，12A - ë ]被开发由市售氟醇（起始1A - d，5，图9a - ë）。使中间体（全氟烷基）烷基碘化物和/或磺酸盐与硫代乙酸钾在DMF中反应，然后通过Zemplén类似反应使所得的硫代乙酸酯脱乙酰。以良好的总收率和高纯度获得了（全氟烷基）链烷硫醇。
• Synthesis of 3-perfluoroalkyl-propyl esters of L-(+)-tartaric acid
  作者：Zoltán Szlávik、Gábor Tárkányi、György Tarczay、Ágnes Gömöry、József Rábai

  DOI：10.1016/s0022-1139(99)00061-5

  日期：1999.9

  A convenient and effective method for the preparation of perfluoroalkyl-propanols (F–(CF2)n–(CH2)3–OH, n = 6,8,10) via boric acid esters is described. The radical addition of F-alkyl iodides to the CC double bonds of triallyl borate is followed by the reduction step using tributylstannane hydride under one-pot conditions. Finally, the mild aqueous deprotection of the alcoholic function completes the

  描述了一种 通过硼酸酯制备全氟烷基丙醇（F-（CF 2）n-（CH 2）3 -OH，n = 6,8,10）的便捷有效的方法。将F-烷基碘自由基自由基加成到三烯丙基硼酸酯的CC双键上，然后在一锅条件下使用三丁基锡氢化物进行还原步骤。最后，温和的乙醇功能脱保护完成了反应，总收率为75-79％。通过气相色谱法测定了这些和其他一些氟代醇的相亲性（f）值，这些值描述了它们的相偏性。F-烷基-丙醇是有用的L-酒石酸氟化酯的合成前体-氟双相转化中的潜在螯合剂。
• Synthesis of novel lipophilic and/or fluorophilic ethers of perfluoro-tert-butyl alcohol, perfluoropinacol and hexafluoroacetone hydrate via a Mitsunobu reaction: Typical cases of ideal product separation
  作者：Dénes Szabó、Ana-Maria Bonto、István Kövesdi、Ágnes Gömöry、József Rábai

  DOI：10.1016/j.jfluchem.2005.01.017

  日期：2005.4

  Fluorophilic ethers having the structure RC(CF(3))(2)O(CH(2))(3)CnF(2n+1) are obtained in high yields, when F-tert-butyl alcohol (R = CF(3)), F-acetone hydrate (R = O(CH(2))(3)C(n)F(2n+1)), F-pinacol (R = C(CF(3))(2)O(CH(2))(3)CnF(2n+1)) are reacted with 3-perfluoroalkyl-1-propanols (C(n)F(2n+1)(CH(2))(3)OH, n = 4, 6, 8, 10) in a Mitsunobu reaction (Ph(3)P/DIAD [i-PrO(2)CN = NCO(2)Pr-i]/ether). The parent lipophilic ethers with the structure of (CF(3))(3)CO(CH(2))(3)CnH(2n+1) were prepared analogously using the corresponding fatty alcohols and F-tert-butyl alcohol. To achieve ideal separations, products were transferred to orthogonal phases relative to the other reaction components using fluorous extraction. fluorous solid-organic liquid filtration, or steam-distillation. Selected physical properties including melting and boiling point, together with fluorous partition coefficients of these ethers were determined and the figures obtained were qualitatively analyzed using relevant thermodynamic theories. Some of these ethers are liquids with rather low freezing points and are miscible with fluorocarbon solvents. (c) 2005 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.