5,5,6,6,7,7,8,8,8-nonafluoro-2-methyloct-3-yn-2-ol | 82721-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5,6,6,7,7,8,8,8-nonafluoro-2-methyloct-3-yn-2-ol
• CAS: 82721-68-4
• 化学式: C₉H₇F₉O
• 分子量: 302.14
• InChiKey: WITWPGGAZCIZSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,5,6,6,7,7,8,8,8-nonafluoro-2-methyloct-3-yn-2-ol 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.17h， 生成 1-(4-nitrophenyl)-4-(perfluorobutyl)-1H-1,2,3-triazole
  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：

  3-iodo-2-methyl-4-perfluorobutylbut-4-en-2-ol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到5,5,6,6,7,7,8,8,8-nonafluoro-2-methyloct-3-yn-2-ol
  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。
• Electrochemical initiation of radical chain addition of F-n butyl iodide to acetylenic alcohols. Cyclic voltammetric investigation of the mechanism
  作者：P. Calas、C. Amatore、L. Gomez、A. Commeyras

  DOI：10.1016/s0022-1139(00)80384-x

  日期：1990.8

  initiation of the radical chain addition of F-n butyl iodide to alkynols through the cathodic reduction of the halide at a carbon cathode is presented. A simplified analysis, based on cyclic voltammetry affords an estimation of the ratio of the rate constants of the two propagation steps, addition of Rf° to alkynol and iodine atom transfer from the F-alkyl iodide to the resulting vinyl radical, involved in

  提出了通过在碳阴极上卤化物的阴极还原引发Fn丁基碘自由基向炔醇的自由基链加成反应。基于循环伏安法的简化分析提供了两个传播步骤速率常数比率的估算值，R f °添加到炔醇中，碘原子从F-烷基碘化物转移到生成的乙烯基，这涉及自由基链机制。
• The rupe reaction applied to 3-(n-perfluorobutyl)alk-2-yn-1-ols: an unexpected route to 5-n-perfluoropropylfuran-3(2H)-ones
  作者：Laurent Gomez、Patrick Calas、Auguste Commeyras

  DOI：10.1039/c39850001493

  日期：——

  Under the conditions of the Rupe reaction hydration of the triple bond of the perfluorobutylalkynols n-C4F9CCCR(Me)OH occur yielding the ketone n-C4F9CH2COCR(Me)OH; this ketone undergoes intramolecular reaction providing an interesting route to 5-n-perfluoropropylfuran-3(2H)-ones.

  在Rupe反应条件下，全氟丁基炔醇的三键水合，生成nC 4 F 9 C CCR（Me）OH，生成酮nC 4 F 9 CH 2 COCR（Me）OH。该酮发生分子内反应，为生成5-n-全氟丙基呋喃-3（2 H）-ones提供了有趣的途径。
• Influence of a perfluorobutyl substituent on the rearrangement of prop-2-ynyl diethylphosphites to allenic phosphonates
  作者：H�l�ne Collet、Patrick Calas、Auguste Commeyras

  DOI：10.1039/c39840001152

  日期：——

  The Prop-2-ynyl diethylphosphites n-C4F9–CC-CR1R2OP(OEt)2 are obtained from the reaction of the corresponding prop-2-ynyl alcohols with diethyl chlorophosphite; the rearrangement of these phosphates into α-perfluorobutylallenic phosphonates is found to depend on the nature of the substituent R1 and R2, and an unexpected HF elimination is found for R1= H, R2= Me.

  丙-2-炔基二乙基亚磷酸酯nC 4 F 9 –C C-CR 1 R 2 OP（OEt）2是由相应的丙-2-炔基醇与亚磷酸二乙酯反应制得的。发现这些磷酸盐重新排列为α-全氟丁基亚烷基膦酸酯取决于取代基R 1和R 2的性质，并且对于R 1 = H，R 2 = Me ，发现了意外的HF消除。