2,2,3,3,4,4-六氟-1-(三氟甲基)氮杂环丁烷 | 16276-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 中文名称: 2,2,3,3,4,4-六氟-1-(三氟甲基)氮杂环丁烷
• 英文名称: perfluoro(1-methylazetidine)
• 英文别名: perfluoro-N-azetidine；2,2,3,3,4,4-Hexafluoro-1-(trifluoromethyl)azetidine
• CAS: 16276-23-6
• 化学式: C₄F₉N
• 分子量: 233.036
• InChiKey: MJDKZEBYLNPVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  0
• 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：
  10

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4-六氟-1-(三氟甲基)氮杂环丁烷 生成 Perfluoro-2-azapropen
  参考文献：
  名称：

  杂环多氟化合物。第十三部分。全氟（四氢-2-甲基-2 H -1,2-恶嗪）与全氟-（3,6-二氢-2-甲基-2 H -1,2-恶嗪）的热反应：全氟-的合成和性质（1-甲基-2-吡咯烷酮），全氟-（1-甲基-2-氧代-3-吡咯啉）和全氟-（1-甲基氮杂环丁烷）

  摘要：

  通过用三氟化钴处理全氟-（3,6-二氢-2-甲基-2 H -1,2-恶嗪）制得的全氟（四氢-2-甲基-2 H -1,2-恶嗪）在20 °C时分解在铂中480–580°产生除其他外的全氟-（1-甲基氮杂环丁烷）和全氟-（1-甲基-2-吡咯烷酮）；当四氢恶嗪在350°C下通过铁时，全氟-（1-甲基-2-吡咯烷酮）是主要产物。同样，全氟-（3,6-二氢-2-甲基-2 H-1,2，-恶嗪）与400°C的铁反应使它发生脱氟环缩合为全氟-（1-甲基-2-氧代-3-吡咯啉）。全氟-（1-甲基-2-吡咯烷酮）与四氟化硫反应生成全氟-（1-甲基吡咯烷），并被碱水溶液降解为四氟琥珀酸。吡咯烷酮的光解或热解得到全氟-（1-甲基氮杂环丁烷），全氟（亚甲基甲胺）和四氟乙烯。全氟-（1-甲基-2-氧代-3-吡咯啉）的氯化得到全氟-（反式-3,4-二氯-1-甲基-2-吡咯烷酮），其与碱水溶液反应生成αβ-二氯二氟琥珀酸

  DOI：

  10.1039/j39670002263
• 作为产物：
  描述：

  N,N-bis(trifluoromethyl)-2bromotetrafluoroethylamine 生成 2,2,3,3,4,4-六氟-1-(三氟甲基)氮杂环丁烷
  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

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.9, 8, page 125 - 158
  作者：

  DOI：——

  日期：——
• Thermal decomposition of halon alternatives
  作者：Takashi Yamamoto、Akio Yasuhara、Fujfo Shiraishi、Kunimitsu Kaya、Takashi Abe

  DOI：10.1016/s0045-6535(97)00126-4

  日期：1997.8

  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.
• Heterocyclic polyfluoro-compounds. Part XIII. Thermal reactions of perfluoro(tetrahydro-2-methyl-2H-1,2-oxazine) and perfluoro-(3,6-dihydro-2-methyl-2H-1,2-oxazine) : synthesis and properties of perfluoro-(1-methyl-2-pyrrolidone), perfluoro-(1-methyl-2-oxo-3-pyrroline), and perfluoro-(1-methylazetidine)
  作者：R. E. Banks、R. N. Haszeldine、V. Matthews

  DOI：10.1039/j39670002263

  日期：——

  ring-contraction to perfluoro-(1-methyl-2-oxo-3-pyrroline). Perfluoro-(1-methyl-2-pyrrolidone) reacts with sulphur tetrafluoride to give perfluoro-(1-methylpyrrolidine), and is degraded to tetrafluorosuccinic acid by aqueous base; photolysis or pyrolysis of the pyrrolidone gives perfluoro-(1-methylazetidine), perfluoro(methylenemethylamine) and tetra-fluoroethylene. Chlorination of perfluoro-(1-methyl-2-oxo-3-pyrroline)

  通过用三氟化钴处理全氟-（3,6-二氢-2-甲基-2 H -1,2-恶嗪）制得的全氟（四氢-2-甲基-2 H -1,2-恶嗪）在20 °C时分解在铂中480–580°产生除其他外的全氟-（1-甲基氮杂环丁烷）和全氟-（1-甲基-2-吡咯烷酮）；当四氢恶嗪在350°C下通过铁时，全氟-（1-甲基-2-吡咯烷酮）是主要产物。同样，全氟-（3,6-二氢-2-甲基-2 H-1,2，-恶嗪）与400°C的铁反应使它发生脱氟环缩合为全氟-（1-甲基-2-氧代-3-吡咯啉）。全氟-（1-甲基-2-吡咯烷酮）与四氟化硫反应生成全氟-（1-甲基吡咯烷），并被碱水溶液降解为四氟琥珀酸。吡咯烷酮的光解或热解得到全氟-（1-甲基氮杂环丁烷），全氟（亚甲基甲胺）和四氟乙烯。全氟-（1-甲基-2-氧代-3-吡咯啉）的氯化得到全氟-（反式-3,4-二氯-1-甲基-2-吡咯烷酮），其与碱水溶液反应生成αβ-二氯二氟琥珀酸