3,3,4,4,5,5,6,6,6-nonafluorohex-1-yne | 59665-30-4

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3,3,4,4,5,5,6,6,6-nonafluorohex-1-yne
• CAS: 59665-30-4
• 化学式: C₆HF₉
• 分子量: 244.06
• InChiKey: BVDUDNZLDHKIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,3,4,4,5,5,6,6,6-nonafluorohex-1-yne 在 copper(ll) sulfate pentahydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 1.17h， 生成 4-(4-(perfluorobutyl)-1H-1,2,3-triazol-1-yl)aniline
  参考文献：
  名称：

  Exploring the Implication of DDX3X in DENV Infection: Discovery of the First-in-Class DDX3X Fluorescent Inhibitor

  摘要：

  In the absence of effective drugs or vaccines for the treatment of the five Dengue Virus serotypes, the search for novel antiviral drugs is of primary importance for the scientific community. In this context, drug repurposing represents the most used strategy; however, the study of host targets is now attracting attention since it allows identification of broad-spectrum drugs endowed with high genetic barrier. In the last ten years our research group identified several small molecules DDX3X inhibitors and proved their efficacy against different viruses including novel emerging ones. Herein, starting from a screening of our compounds, we designed and synthesized novel derivatives with potent activity and high selectivity. Finally, we synthesized a fluorescent inhibitor that allowed us to study DDX3X cellular localization during DENV infection in vitro. Immunofluorescence analysis showed that our inhibitor colocalized with DDX3X, promoting the reduction of infected cells and recovering the number of viable cells.

  DOI：

  10.1021/acsmedchemlett.9b00681
• 作为产物：
  描述：

  在 氢氧化钾 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3,3,4,4,5,5,6,6,6-nonafluorohex-1-yne
  参考文献：
  名称：

  一种高效的全氟烷基炔烃电化学途径

  摘要：

  将全氟烷基碘电催化加成到3-羟基-3-烷基丁-1-炔中，然后在碱性介质中进行加氢碘化和热裂解，可以轻松有效地制备（全氟烷基）炔。

  DOI：

  10.1039/c39820000433

文献信息

• [EN] USE OF DDX3 INHIBITORS AS ANTIPROLIFERATIVE AGENTS<br/>[FR] UTILISATION D'INHIBITEURS DE DDX3 EN TANT QU'AGENTS ANTIPROLIFÉRATIFS
  申请人：AZIENDA OSPEDALIERA UNIV SENESE

  公开号：WO2017162834A1

  公开（公告）日：2017-09-28

  The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II)

  这项发明涉及具有DDX3抑制活性的I或II式化合物，相关的药物组合物以及它们作为抗高增殖剂的用途。(I)或(II)
• [EN] HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS D'HÉLICASE DDX3 HUMAINE COMME AGENTS THÉRAPEUTIQUES
  申请人：AZIENDA OSPEDALIERA UNIV SENESE

  公开号：WO2016128541A1

  公开（公告）日：2016-08-18

  The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.

  本发明涉及具有RNA解旋酶DDX3抑制活性的化合物I和II的公式及其治疗用途，特别是用于治疗病毒性疾病。
• Selective Synthesis of Perfluoroalkylated Corannulenes and Investigation of their Structural, Dynamic and Electrochemical Behavior
  作者：Axel Haupt、Lisa-Marie Keller、Maximilian Kutter、Dieter Lentz

  DOI：10.1002/chem.201801021

  日期：2018.7.25

  Herein we report general methods allowing the synthesis of various perfluoroalkylated corannulenes with a specific substitution pattern. Variable temperature NMR spectroscopic investigations revealed dynamic behavior which was analyzed by line shape analysis. The activation parameters of these dynamic processes were determined. For a tetrasubstituted compound it was possible to observe through space

  本文中，我们报告了通用方法，可以合成具有特定取代模式的各种全氟烷基化Corannulenes。可变温度NMR光谱研究揭示了动态行为，其通过线形分析进行了分析。确定了这些动态过程的激活参数。对于四取代的化合物，有可能通过空间标量耦合进行观察。X射线晶体学阐明了堆积基序，表明取代模式和取代基的大小强烈影响分子间π堆积。通过循环伏安法测定全氟烷基化化合物的还原电势。
• Reaction of (perfluoroalkyl)alkynes with iodine and some of its derivatives
  作者：Patrice Moreau、Auguste Commeyras

  DOI：10.1039/c39850000817

  日期：——

  Iodine and some of is derivatives, such as ICI, ICN, and IF, react, under relatively mild conditions, with (perfluoroalkyl)alkynes RF–CC–H to afford regiospecifically the corresponding 1-iodo perfluorinated alkenes.

  碘和某些衍生物（例如ICI，ICN和IF）在相对温和的条件下与（全氟烷基）炔烃R F – C C–H反应，以区域特异性地提供相应的1-碘全氟烯烃。
• Fluoro-Ene Reaction Versus [2+2] Cycloaddition in the Thermal C²-C⁶Cyclization of Enyne-Allenes: An Experimental and Theoretical Investigation
  作者：M. Emin Cinar、Chandrasekhar Vavilala、Ralph Jaquet、Jan W. Bats、Michael Schmittel

  DOI：10.1002/ejoc.201402438

  日期：2014.8

  A series of fluoroalkyl-substituted enyne-allenes have been synthesized by a new route with the aim of elucidating the possibility of a fluoro-ene reaction via an intermediate fulvenyl diradical generated in the thermal C2–C6 (Schmittel) cyclization reaction. As a result of the strong C–F bond, fluorine atom transfer was not observed. Instead, 1H-cyclobuta[a]indenes were formed in good yields despite

  一系列氟代烷基取代的烯炔-丙二烯通过新途径合成，目的是阐明氟烯反应的可能性，该反应通过在热 C2-C6（施密特尔）环化反应中产生的中间体富烯基双自由基进行。由于强 C-F 键，没有观察到氟原子转移。相反，尽管应变能很高，但仍以良好的产率形成了 1H-环丁 [a] 茚。B3LYP 理论水平的 DFT 计算表明，尽管氟-烯反应是可用的放热反应最多的反应，但在各种模型化合物中，环丁烯的形成在动力学上比 [1,5]-氟位移 5-15 kcal mol-1 更有利.