2,2,3,3,4,4,5,5-八氟-1-(五氟乙基)-吡咯烷 | 78159-15-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,2,3,3,4,4,5,5-八氟-1-(五氟乙基)-吡咯烷
• 英文名称: perfluoro(N-ethylpyrrolidine)
• 英文别名: Pyrrolidine, 2,2,3,3,4,4,5,5-octafluoro-1-(pentafluoroethyl)-；2,2,3,3,4,4,5,5-octafluoro-1-(1,1,2,2,2-pentafluoroethyl)pyrrolidine
• CAS: 78159-15-6
• 化学式: C₆F₁₃N
• 分子量: 333.052
• InChiKey: UMGCTGRNIYHTCR-UHFFFAOYSA-N

物化性质

• 沸点：
  47-49 °C
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,5,5-八氟-1-(五氟乙基)-吡咯烷 在 硫酸 作用下， 反应 24.0h， 以65.3%的产率得到perfluoro(N-ethyl-2-oxo-pyrrolidine)
  参考文献：
  名称：

  通过全氟（N-烷基环胺）与发烟硫酸反应形成OP全氟（N-烷基内酰胺）

  摘要：

  全氟（N-烷基环胺）与发烟硫酸反应以高收率获得了全氟（N-烷基内酰胺）。

  DOI：

  10.1246/cl.1985.375
• 作为产物：
  描述：

  全氟三乙胺 生成 2,2,3,3,4,4,5,5-八氟-1-(五氟乙基)-吡咯烷
  参考文献：
  名称：

  Thermal decomposition of halon alternatives

  摘要：

  2H-Heptafluoropropane, trifluoroiodomethane, trifluorobromomethane, perfluorotriethylamine, N,N-bis(trifluoromethyl>2H-tetrafluoroethylamine, N,N-bis(trifluoromethyl)-2-bromotetrafluoroethylamine, perfluorodimethylvinylamine, and perfluoro-N-ethylpyrrolidine were pyrolyzed in order to evaluate their thermal behavior in fire fighting. Fluorinated compounds containing iodine or bromine atoms decomposed easier than perfluorcompounds containing none of them. There seemed not to be any differences of thermal stability between perfluorotrialkylamines and perfluorinated hydrocarbons. A large amount of hydrogen fluoride was produced from any fluorinated compounds by pyrolysis. Also, thermal decomposition of fluorinated nitrogen-containing compounds generated high concentration of nitrogen oxides. Organic products of thermal decomposition were analyzed by gas chromatography-mass spectrometry. Main products from 2H-heptafluoropropane and perfluorotriethylamine were identified to be perfluoroisobutane and perfluorinated N-ethylpyrrolidine, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0045-6535(97)00126-4

文献信息

• The electrochemical fluorination of N-containing carboxylic acids (Part 4). Fluorination of methyl 3-dialkylamino-isobutyrates and methyl 3-dialkylamino-n-butyrates
  作者：Takashi Abe、Haruhiko Fukaya、Eiji Hayashi、Yoshio Hayakawa、Masakazu Nishida、Hajime Baba

  DOI：10.1016/0022-1139(93)03019-i

  日期：1994.2

  Several methyl esters of 3-dialkylamino-substituted n- and isobutyric acids have been subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides. Dimethyl, diethyl, pyrrolidino, morpholino, piperidino and N-methylpiperazino groups were investigated as dialkylamino substituents. The structure/yield relationship was evaluated both in terms of the structure of the acid and

  3-二烷基氨基取代的正丁酸和异丁酸的几种甲酯已经进行了电化学氟化反应，得到了相应的全氟代氟化物。研究了作为二烷基氨基取代基的二甲基，二乙基，吡咯烷基，吗啉代，哌啶子基和N-甲基哌嗪子基团。分别根据酸的结构和氨基的种类评价了结构/产率关系。由具有异丁酸骨架的甲酯比具有正丁酸基团的甲酯得到的全氟氟化物的收率更高，并且由具有环状氨基的酸得到的无氟氟化物的收率更高。
• The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of methyl esters of 3-dialkylamino propionic acids
  作者：Takashi Abe、Eiji Hayashi、Haruhiko Fukaya、Yoshio Hayakawa、Hajime Baba、Shigeki Ishikawa、Kinya Asahino

  DOI：10.1016/s0022-1139(00)82821-3

  日期：1992.4

  Six methyl esters of 3-dialkylamino-substituted propionic acids were subjected to electrochemical fluorination to give the corresponding perfluoroacid fluorides. The following dialkylamino substituents were investigated: diethylamino, di-n-propyl-amino, di-n-butylamino, pyrrolidino, morpholino and piperidino groups. These perfluoroacid fluorides, which were obtained in fair yields, are considered to

  将3-二烷基氨基取代的丙酸的六种甲酯进行电化学氟化，得到相应的全氟代氟化物。研究了以下二烷基氨基取代基：二乙基氨基，二正丙基氨基，二正丁基氨基，吡咯烷基，吗啉代和哌啶子基。这些以合理收率获得的全氟酸氟化物被认为是制备软质（可降解）含氟化合物的潜在关键前体。这些盐在水溶液中显示出明显降低的表面张力。报告了所获得的所有全氟酸氟化物的物理性质，以及它们的光谱数据（19 F NMR，质谱和IR光谱）。
• The electrochemical fluorination of nitrogen-containing carboxylic acids. Fluorination of methyl esters of cyclic amino-group substituted carboxylic acids
  作者：Takashi Abe、Eiji Hayashi、Haruhiko Fukaya、Hajime Baba

  DOI：10.1016/s0022-1139(00)80494-7

  日期：1990.11

  Nine methyl esters of cyclic amino-group substituted carboxylic acids related to glycine, alanine or β-alanine were subjected to electrochemical fluorination. This afforded the corresponding perfluoroacid fluorides together with cleavage products in fair yields. As cyclic amino-substituents, pyrrolidino-, morpholino-, piperidino-, hexamethyleneimino- and N′-methyl-piperazinyl-groups were investigated

  对与甘氨酸，丙氨酸或β-丙氨酸有关的环状氨基取代的羧酸的九种甲酯进行电化学氟化。这样以合理的产率得到了相应的全氟氟化物和裂解产物。作为环状氨基取代基，研究了吡咯烷基，吗啉代，哌啶子基，六亚甲基亚氨基和N'-甲基哌嗪基。未观察到环化副产物的形成，这与脂族二烷基氨基取代的羧酸的氟化形成对比。从这样的2-环氨基丙酸甲酯[环氨基：吡咯烷基，吗啉代或哌啶子基]，与全氟酸氟化物一起得到全氟甲基酯，产率为1-2％和14-29。 ％ 分别。前一种化合物的形成归因于庞大的环状氨基的阻断作用。报告了所获得的新化合物的物理性质及其光谱（19 F NMR，质量和IR）数据。
• Highly fluorinated heterocycles part XV [1]. The metal catalysed defluorinative rearrangement of polyfluorinated pyrrolidines to polyfluoropyridines
  作者：P.L. Coe、J.H. Sleigh

  DOI：10.1016/s0022-1139(00)81785-6

  日期：1981.4

  Pyrolysis of a number of polyfluoro-1-alkyl pyrrolidines over iron gauze at 500–525° affords a small conversion to polyfluoropyridines.

  许多多氟-1-烷基吡咯烷在500-525°C的铁丝网上热解后，少量转化为多氟吡啶。
• The reaction of perfluoro (N-alklyl-cyclic amines) with oleum. The formation and characterization of perfluorolactams
  作者：Eiji Hayashi、Takashi Abe、Shunji Nagase

  DOI：10.1016/s0022-1139(00)81545-6

  日期：1988.11

  Treatment of several kinds of perfluoro (N-alkyl-cyclic amines) (-pyrrolidines, -morpholines, -piperidines and -hexahydroazepin) with oleum at 140 ∼ 170 °C afforded the corresponding perfluorolactams in fair yields. The reaction conditions and the properties of perfluorolactams are described.

  在140〜170℃下，用发烟硫酸处理几种全氟（N-烷基环胺）（-吡咯烷，-吗啉，-哌啶和-六氢pin庚啶），以适当的收率得到相应的全氟内酰胺。描述了全氟内酰胺的反应条件和性质。