chloroperfluoro-1-hexene | 31001-56-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: chloroperfluoro-1-hexene
• 英文别名: 6-chloro-6H-undecafluoro-hex-1-ene；6-Chlorundecafluorhex-1-en；6-Chloroperfluoro-1-hexen；6-Chloroperfluorohex-1-ene；6-chloro-1,1,2,3,3,4,4,5,5,6,6-undecafluorohex-1-ene
• CAS: 31001-56-6
• 化学式: C₆ClF₁₁
• 分子量: 316.501
• InChiKey: IXVAHJDLGHPNSM-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C
• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 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：
  11

反应信息

• 作为反应物：
  描述：

  chloroperfluoro-1-hexene 在 potassium fluoride 、 ammonium peroxydisulfate 、 sodium formate 、 氯 作用下， 以 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 Sodium;1,1,2,2-tetrafluoro-2-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoropentadecoxy)ethanesulfonate
  参考文献：
  名称：

  A redox-initiated per(poly)fluoroalkylation of olefins by per(poly)fluoroalkyl chlorides

  摘要：

  The per(poly)fluoroalkylation of olefins by per(poly)fluoroalkyl chlorides, initiated by ammonium persulfate/sodium formate (NH4)2S2O8/HCO2Na), is described. The reaction proceeds smoothly in polar aprotic solvents. The presence of functional groups like sodium carboxylate or sulfonate in the polyfluoroalkyl chloride appear to facilitate the reaction. The reaction appears to be initiated by a single-electron transfer, represents the first example of the reactivity of per(poly)fluoroalkyl chlorides, and also demonstrates their use as per(poly)fluoroalkylating agents. For alpha-chloro-omega-iodoperfluoroalkanes only the carbon-iodine bond is cleaved during the reaction. An explanation for the apparent stability of the carbon-chlorine bond in such compounds is given.

  DOI：

  10.1021/jo00022a025
• 作为产物：
  描述：

  1-氯-1,1,2,2,3,3,4,4,5,5,6,6-十二氟-6-碘己烷 以81%的产率得到
  参考文献：
  名称：

  ZHANG, YUAN-FA;GUO, CAI-YUN;ZHOU, XIN-YUE;CHEN, QING-YUN, ACTA CHIM. SIN., 1982, 40, N 4, 331-336

  摘要：

  DOI：

文献信息

• Studies on fluoroalkylation and fluoroalkoxylation. Part 24. Magnesium-induced single electrons transfer in reactions of fluoroalkyl iodides with alkenes and alkynes
  作者：Qing-Yun Chen、Zai-Ming Qiu、Zhen-Yu Yang

  DOI：10.1016/s0022-1139(00)81022-2

  日期：1987.7

  and the reaction could be inhibited by p-DNB. All these results seem to show that a radical mechanism is involved in non-ethereal solvents. However, both radical addition and fluroalkyl Grignard reagent reactions are involved in THF. The formation of fluoroalkylmagnesium iodide is also found to proceed through a radical intermediate.

  金属镁催化全氟烷基碘化物与烯烃和炔烃的自由基反应，在温和的条件下以高收率得到相应的加合物。1,4-二硝基苯（p-DNB）或氧气的存在不会影响反应，但是氢醌可以部分抑制反应，而2-亚硝基则可以完全抑制反应。DMF中的2-硝基丙烷。在THF中，除了正常的加合物外，还可以得到氟代烯烃，并且该反应可以被p-DNB抑制。所有这些结果似乎表明，自由基机理涉及非醚溶剂。但是，THF中涉及自由基加成反应和氟烷基格氏试剂反应。还发现氟烷基碘化镁的形成是通过自由基中间体进行的。
• GUO, CAI-YUN;ZHANG, YUAN-FA;CHEN, QING-YUN, ACTA CHIM. SIN., 1982, 40, N 9, 828-834
  作者：GUO, CAI-YUN、ZHANG, YUAN-FA、CHEN, QING-YUN

  DOI：——

  日期：——
• HUANG WEI-YUAN; WANG WEI, ACTA CHIM. SIN., 44,(1986) N 9, 940-945
  作者：HUANG WEI-YUAN、 WANG WEI

  DOI：——

  日期：——
• CHEN QING-YUN; QIU ZAI-MING; YANG ZHEN-YU, J. FLUOR. CHEM., 36,(1987) N 2, 149-161
  作者：CHEN QING-YUN、 QIU ZAI-MING、 YANG ZHEN-YU

  DOI：——

  日期：——
• A redox-initiated per(poly)fluoroalkylation of olefins by per(poly)fluoroalkyl chlorides
  作者：Changming Hu、Fengling Qing

  DOI：10.1021/jo00022a025

  日期：1991.10

  The per(poly)fluoroalkylation of olefins by per(poly)fluoroalkyl chlorides, initiated by ammonium persulfate/sodium formate (NH4)2S2O8/HCO2Na), is described. The reaction proceeds smoothly in polar aprotic solvents. The presence of functional groups like sodium carboxylate or sulfonate in the polyfluoroalkyl chloride appear to facilitate the reaction. The reaction appears to be initiated by a single-electron transfer, represents the first example of the reactivity of per(poly)fluoroalkyl chlorides, and also demonstrates their use as per(poly)fluoroalkylating agents. For alpha-chloro-omega-iodoperfluoroalkanes only the carbon-iodine bond is cleaved during the reaction. An explanation for the apparent stability of the carbon-chlorine bond in such compounds is given.