(3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane | 1464148-71-7

• 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: (3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane
• CAS: 1464148-71-7
• 化学式: C₁₂H₁₄F₉I
• 分子量: 456.133
• InChiKey: LBOAVJIKQMPRPT-UHFFFAOYSA-N

物化性质

• 沸点：
  267.5±40.0 °C(Predicted)
• 密度：
  1.651±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• 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：
  9

反应信息

• 作为产物：
  描述：

  乙烯基环己烷 、 全氟碘代丁烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以79%的产率得到(3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane
  参考文献：
  名称：

  通过丙酮和氟代烷基碘化物之间的非共价相互作用促进了普通的绿色氟代烷基化反应。

  摘要：

  提出了通过丙酮和氟代烷基碘之间的非共价相互作用引发的可见光促进的氟代烷基化反应的第一个例子。该反应系统具有合成简单，反应条件温和，无任何光氧化还原催化剂和高官能团耐受性的特点。各种各样的底物范围，如烯烃，炔烃和（杂）芳烃都与反应体系兼容。

  DOI：

  10.1039/c9cc09517a

文献信息

• Radical Addition of Perfluoroalkyl Iodides to Alkenes and Alkynes Initiated by Sodium Dithionite in an Aqueous Solution in the Presence of a Novel Fluorosurfactant
  作者：Zhiwei Xiao、Huawei Hu、Jiaoli Ma、Qingyun Chen、Yong Guo

  DOI：10.1002/cjoc.201300433

  日期：2013.7

  fluoroalkylation to occur in the water without adding organic solvent. The addition of perfluoroalkyl iodides with olefins and alkynes under the initiation of Na2S2O4 in water in the presence of the fluorosurfactant gave the corresponding adducts in good to excellent yields. The fluorosurfactant was suitable for a radical addition process.

  制备并表征了一种新型的氟化阴离子表面活性剂Cl（CF 2）6 O（CF 2）2 SO 3 N（C 2 H 5）4。含氟表面活性剂的应用使氟烷基化在水中发生而无需添加有机溶剂。在含氟表面活性剂的存在下，在水中在Na 2 S 2 O 4的引发下，将全氟烷基碘化物与烯烃和炔烃加成，得到相应的加合物，收率良好或优异。含氟表面活性剂适用于自由基加成过程。
• Mechanistic Insights into FLP‐Catalyzed Iodoperfluoroalkylations
  作者：Michael Spittler、Lucas Helmecke、Constantin Czekelius

  DOI：10.1002/ejoc.201800866

  日期：2019.1.23

  The frustrated Lewis pair‐catalyzed iodoperfluoroalkylation of olefins, its substrate activation mode, and catalyst degradation pathways are mechanistically investigated by kinetic measurements. The transformation most likely proceeds via coordination of the phosphane to the perfluoroalkyl iodide and involves radical intermediates.

  通过动力学测量机制研究了受挫的路易斯对催化的烯烃碘全氟烷基化反应，其底物活化方式和催化剂降解途径。该转化最可能通过膦与全氟烷基碘的配位而进行，并涉及自由基中间体。
• Perfluoroalkylation of Alkenes by Frustrated Lewis Pairs
  作者：Ilona Behrends、Susanne Bähr、Constantin Czekelius

  DOI：10.1002/chem.201604414

  日期：2016.11.21

  The activation of perfluoroalkyl iodides by the frustrated Lewis pair tris(pentafluorophenyl)borane and tri‐tert‐butylphosphine is described. By abstraction of both a fluorine and an iodine atom, an iodophosphonium fluoroborate salt is formed. In the presence of alkenes the corresponding iodoperfluoroalkylation products are generated regioselectively. First mechanistic investigations support a radical

  由受挫路易斯对三（五氟苯基）硼烷和三-全氟烷基碘的激活叔丁基膦进行说明。通过同时提取氟和碘原子，形成氟硼酸碘i盐。在烯烃的存在下，区域选择性地产生相应的碘全氟烷基化产物。最初的机械研究支持一种激进的机制。
• Process for preparing fluorine-containing carboxylic acid ester
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0252736B1

  公开（公告）日：1991-07-24
• Metal-Free Activation of C–I Bonds and Perfluoroalkylation of Alkenes with Visible Light Using Phosphine Catalysts
  作者：Lucas Helmecke、Michael Spittler、Kai Baumgarten、Constantin Czekelius

  DOI：10.1021/acs.orglett.9b02812

  日期：2019.10.4

  An efficient metal-free, photomediated iodo perfluoroalkylation under mild conditions was developed. Using catalytic amounts (10 mol %) of phosphines and blue light irradiation, various olefins are transformed into the corresponding addition products within short reaction times. For this purpose, a modular and convenient 3D printed photoreactor was constructed, which is presented as an open source model. The reaction presumably proceeds upon generation of perfluoroalkyl radicals, which are formed by catalyst-induced absorption enhancement.