1H,1H,2H,2H,3H,3H-perfluorotridecyl iodide | 541547-94-8

• 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,3H,3H-perfluorotridecyl iodide
• 英文别名: 1H,1H,2H,2H,3H,3H-perflurotridecyl iodide；1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-Henicosafluoro-13-iodotridecane；1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-henicosafluoro-13-iodotridecane
• CAS: 541547-94-8
• 化学式: C₁₃H₆F₂₁I
• 分子量: 688.062
• InChiKey: JYADHEPYZFNKON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  1H,1H,2H,2H,3H,3H-perfluorotridecyl iodide 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以88%的产率得到13-azido-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-henicosafluorotridecane
  参考文献：
  名称：

  方便地以克数合成纯氟烷基叠氮化物

  摘要：

  F-烷基化试剂的反应，包括（全氟烷基）烷基卤化物和磺酸盐[R fn（CH 2）m X（X = Br，I，OTs，OTf）]，以及在100°C DMSO中略有过量的NaN 3保持5小时，然后进行水蒸气蒸馏，以高纯度（GC测定≥98％）高至极好产率分离出叠氮化物R fn（CH 2）m N 3。由于这些氟叠氮化物的稳定性，它们可以在大气压或更低的压力下蒸馏以进一步纯化。4-叠氮全氟甲苯（p- CF 3 C 6 F 4 N 3）和1-叠氮辛烷也分别在相似的条件下从全氟甲苯（CF 3 C 6 F 5）或1-碘辛烷开始制备。蒸汽蒸馏可以轻松安全地分离出高达50 g的产品。

  DOI：

  10.1016/j.jfluchem.2016.08.005
• 作为产物：
  描述：

  1-碘全氟癸烷 在 咪唑 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1H,1H,2H,2H,3H,3H-perfluorotridecyl iodide
  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

• Enantiopure Fluorous Bis(oxazolines):  Synthesis and Applications in Catalytic Asymmetric Reactions
  作者：Jerome Bayardon、Denis Sinou

  DOI：10.1021/jo049853q

  日期：2004.4.1

  Various enantiopure fluorous bis(oxazolines) with fluorine content between 52.7 and 58.7% have been synthesized by a simple reaction sequence that involved the introduction of two fluorinated ponytails by alkylation of the corresponding nonfluorous bis(oxazolines). These new ligands have been used in palladium-catalyzed alkylation of rac-(E)-1,3-diphenylpropenyl acetate with carbon nucleophiles and

  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。
• 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。
• Polyfluoroalkyl Chain‐Based Assemblies for Biomimetic Catalysis
  作者：Ning Liu、Ping Gao、Hai‐Yan Lu、Lei Fang、Julien Nicolas、Tâp Ha‐Duong、Jiang‐Shan Shen

  DOI：10.1002/chem.202302669

  日期：2024.1.2

  Amphiphobic fluoroalkyl chains are exploited for creating robust and diverse self‐assembled biomimetic catalysts. Long terminal perfluoroalkyl chains (C_nF_2n+1 with n=6, 8, and 10) linked with a short perhydroalkyl chains (C_mH_2m with m=2 and 3) were used to synthesize several 1,4,7‐triazacyclononane (TACN) derivatives, C_nF_2n+1‐C_mH_2m‐TACN. In the presence of an equimolar amount of Zn²⁺ ions that coordinate the TACN moiety and drive the self‐assembly into micelle‐like aggregates, the critical aggregation concentration of polyfluorinated C_nF_2n+1‐C_mH_2m‐TACN⋅Zn²⁺ was lowered by ∼1 order of magnitude compared to the traditional perhyroalkyl counterpart with identical carbon number of alkyl chain. When 2’‐hydroxypropyl‐4‐nitrophenyl phosphate was used as the model phosphate substrate, polyfluorinated C_nF_2n+1‐C_mH_2m‐TACN⋅Zn²⁺ assemblies showed higher affinity and catalytic activity, compared to its perhyroalkyl chain‐based counterpart. Coarse‐grained molecular dynamic simulations have been introduced to explore the supramolecular assembly of polyfluoroalkyl chains in the presence of Zn²⁺ ions and to better understand their enhanced catalytic activity.

  摘要利用疏亲水的氟烷基链来创建稳健、多样的自组装仿生催化剂。长的末端全氟烷基链（CnF2n+1，n=6、8 和 10）与短的全氢烷基链（CmH2m，m=2 和 3）连接，用于合成几种 1,4,7-三氮杂环壬烷（TACN）衍生物 CnF2n+1-CmH2m-TACN。等摩尔量的 Zn2+ 离子能配位 TACN 分子并促使其自组装成胶束状聚集体，在这种情况下，多氟 CnF2n+1-CmH2m-TACN⋅Zn2+ 的临界聚集浓度与烷基链碳数相同的传统全烷基对应物相比降低了∼1 个数量级。当以 2'-hydroxypropyl-4-nitrophenyl phosphate 为模型磷酸盐底物时，多氟 CnF2n+1-CmH2m-TACN⋅Zn2+ 组合物与其基于全烷基链的对应物相比，显示出更高的亲和力和催化活性。我们引入了粗粒度分子动力学模拟，以探索多氟烷基链在 Zn2+ 离子存在下的超分子组装，并更好地理解其增强的催化活性。
• Nanocompartmentalization of Soft Materials with Three Mutually Immiscible Solvents: Synthesis and Self-Assembly of Three-Arm Star-Polyphiles
  作者：Liliana de Campo、Minoo J. Moghaddam、Trond Varslot、Nigel Kirby、Rainer Mittelbach、Tim Sawkins、Stephen T. Hyde

  DOI：10.1021/cm503981t

  日期：2015.2.10

  We report synthesis, thermotropic, and lyotropic mesomorphism of a family of novel star-polyphiles: small star-shaped molecules bearing three mutually immiscible arms, hydrophilic (oligoethylene glycol), oleophilic (alkanes), and fluorophilic (perfluorinated alkanes), attached to a central 1,3,5-trihydroxybenzene core. A facile, flexible multistep synthesis giving high-purity yields of 14 distinct members of the family is described, with variable arm lengths, forming crystalline, or various mesostructured gel phases in their neat state at room temperature. Furthermore, we show that specific members of these star-polyphiles can be simultaneously loaded with up to three mutually immiscible solvents, dodecane, perfluoro-nonane, and water, to form liquid crystals and microemulsions with multiple chemically distinct mesoscale compartments. The mesoscale chemical polyfunctionality of these polyphiles, coupled with thermotropic and lyotropic polymorphism, make them promising potential soft materials for a variety of applications, including host matrices for multiple mutually immiscible chemicals and drug delivery.
• Fluorous chiral bisoxazolines. Synthesis and applications to an asymmetric allylic alkylation
  作者：Jerome Bayardon、Denis Sinou

  DOI：10.1016/s0040-4039(02)02851-4

  日期：2003.2

  The easily accessible fluorous bisoxazolines 3a-b bearing two fluorous ponytails are efficient ligands in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate with carbonucleophiles in benzotrifluoride or CH2Cl2, enantioselectivities of up to 95% being obtained. The ligand is easily separated from the reaction mixture by simple extraction with a fluorous solvent. (C) 2003 Elsevier Science Ltd. All rights reserved.