全氟-2,5-二氮杂己烷-2,5-二氧基 | 36525-64-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 中文名称: 全氟-2,5-二氮杂己烷-2,5-二氧基
• 英文名称: perfluoro-2,5-diazahexane 2,5-dioxyl
• 英文别名: Perfluor-2,5-diazahexan-2,5-dioxyl；Oxo-[1,1,2,2-tetrafluoro-2-[oxido(trifluoromethyl)amino]ethyl]-(trifluoromethyl)azanium；oxo-[1,1,2,2-tetrafluoro-2-[oxido(trifluoromethyl)amino]ethyl]-(trifluoromethyl)azanium
• CAS: 36525-64-1
• 化学式: C₄F₁₀N₂O₂
• 分子量: 298.04
• InChiKey: DODHNLSDGIUFMM-UHFFFAOYSA-N

物化性质

• 沸点：
  54-55

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  8.5
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  全氟-2,5-二氮杂己烷-2,5-二氧基 在 trimethylvinylsilane 作用下， 反应 13.0h， 以9%的产率得到Perfluoro-2-azapropen
  参考文献：
  名称：

  Reaction of bis(trifluoromethyl)amino-oxyl with alkylchlorosilanes and allyldichloro(methyl)silane and of perfluoro-2,5-diazahexane 2,5-dioxyl with vinylsilanes and hydrolysis of the products

  摘要：

  Treatment of the silanes MeSiHCl2, Me2SiHCl and EtSiMeCl2 with the oxyl (CF3)2NO. (1) gives the substitution products (CF3)2NOSiMeCl2 (4) and (CF3)2NOSiMe2Cl (5), and a mixture of (CF3)2NOCHMeSiMeCl2 (8) and (CF3)2NOCH2CH2SiMeCl2 (9) (ratio 20:37), respectively, while the silane EtSiMe2Cl affords mainly the ester (CF3)2NO2CMe (7). Attack of oxyl 1 on the silane CH2 = CHCH2SiMeCl2 results in both allylic substitution and addition to give the compounds CH2 = CHCH(SiMeCl2)ON(CF3)2 (14) and (CF3)2NOCH2CH(CH2SiMeCl2)ON(CF3)2 (15) (ratio 56:40). Reaction of the dioxyl . ON(CF3)CF2CF2N(CF3)O. (2) with the vinylsilanes CH2 = CHSiX3 (X3 = Me3, Cl3, MeCl2) gives mainly 1:1 copolymers [ON(CF3)CF2CF2N(CF3)OCH2CH(SiX3)]n (17), although the cyclic 1:1 adduct ON(CF3)CF2CF2N(CF3)OCH2CHSiMeCl2 (18) is also formed in low yield.Hydrolysis of the silanes 15, (CF3)2NOCH2CH(SiMeCl2)ON(CF3)2 (19a) and (CF3)2NOCH2CH(SiCl3)ON(CF3)2 (19b) affords the corresponding polysiloxanes 24 and 25, and the polysilsesquioxane 26, respectively; the polymers 25 and 26 undergo rearrangement of the type -CH(Si)ON(CF3)2 --> -CH(OSi)N(CF3)2 on storage. The 1:1 copolymers 17b (X3 = MeCl2) and 17c (X3 = Cl3) are also hydrolysed to the corresponding siloxane and silsesquioxane polymers. In contrast, hydrolysis of the compounds 4, 5 and (CF3)2NOCH2CH(OSiX3)N(CF3)2 (20a; X3 = MeCl2) and (20b; X3 = Cl3) results in Si-O bond cleavage.

  DOI：

  10.1016/0022-1139(93)02976-l

文献信息

• The reactions of mercury(II) perfluoro-2,5-diazahexane 2,5-dioxyl and perfluoro-2,5-diazahexane-2,5-diol with halogenoalkanes, acid chlorides and dichlorosilanes
  作者：Michael J. Green、Anthony E. Tipping

  DOI：10.1016/0022-1139(93)02914-z

  日期：1994.3

  Me2SiCl2 and CH2CH2CH2SiCl2, the products are the seven-membered ring heterocycle ON(CF3)2CF2CF2N(CF3)OSiMe2 and the spiro compound ON(CF3)CF2CF2N(CF3)OSiCH2CH2CH2, respectively. Perfluoro-2,5-diazahexane-2,5-diol (3) undergoes reactions with the halides Me2SiCl2 and CF3COCl in the presence of quinoline to give the same products as formed from mercurial 2, but reaction does not take place with iodoethane;

  用卤代烷烃MeI，MeBr和EtI或酰氯MeCOCl和CF 3 COCl处理标题汞（2），得到化合物RON（CF 3）CF 2 CF 2 CF 2 N（CF 3）OR（RMe， Et，MeCO和CF 3 CO）的收率良好；卤化物CF 3 CH 2 I或BrCH 2 CH 2 Br不会发生反应。涉及二碘代烷烃CH 2 I 2和ICH 2 CH 2 CH 2 I的反应得到杂环ON（CF3）CF2CF2N（ OCH2）和共聚物[ON（CF 3）CF 2CF 2 N（CF 3）OCH 2 CH 2 CH 2 ] n分别为二氯硅烷Me 2 SiCl 2和CH2CH2CH2SiCl 2的产物，它们是七元环杂环ON（ ）2CF2CF2N（ ）OSiMe2和螺环化合物分别为ON（ ）CF2CF2N（ ）OSiCH2CH2CH 2。全氟2,5-二氮杂己烷-2,5-二醇（3）在喹啉存在下与卤化物Me
• ‘Living’ free-radical copolymers prepared from perfluoro-2,5-diazahexane-2,5-dioxyl
  作者：Ahmad Arfaei、Robert N. Haszeldine、Sydney Smith

  DOI：10.1039/c39760000260

  日期：——

  Stable, ‘living’, free-radical copolymers with number-average molecular weights in the range 1250–11,000, prepared by reaction of an excess of perfluoro-2,5-diazahexane-2,5-dioxyl with fluoro-olefins, react, via the terminal nitroxide groups, with fluoro-, sulphur dioxide, or perfluorobuta-1,3-diene to give copolymers of enhanced molecular weights; unsaturated nitroso rubbers prepared by reaction of

  通过使过量的全氟-2,5-二氮杂己烷-2,5-二氧基与氟代烯烃反应制得的，数均分子量在1250–11,000范围内的稳定的“活性”自由基共聚物，通过末端的氮氧化物基团，与氟，二氧化硫或全氟丁1,3-二烯形成分子量提高的共聚物；通过预氟代-1,3-二烯与六氟丙烯和二氧基制备的“活性”共聚物反应制得的不饱和亚硝基橡胶已成功地与“活性”共聚物交联。
• Some oxidative-addition reactions of the diradical, perfluoro-NN′-dimethylethane-1,2-bis(amino-oxyl), CF₃N(O)CF₂CF₂N(O)CF₃, with iridium(<scp>I</scp>) and platinum(<scp>0</scp>) complexes
  作者：Brian L. Booth、Robert N. Haszeldine、Robert G. G. Holmes

  DOI：10.1039/dt9820000671

  日期：——

  The stable diradical CF3N(O)CF2CF2N(O)CF3 reacts with trans-[IrCl(CO)L2](L = PPh3, AsPh3, or PMePh2), trans-[IrON(CF3)2}(CO)(PPh3)2], and [Pt(PPh3)4] to form the seven-membered ring metallacyclic complexes [[graphic omitted]Cl(CO)L2], [[graphic omitted]ON(CF3)2}(CO)(PPh3)2], and [[graphic omitted](PPh3)2] respectively.

  稳定的双自由基CF 3 N（O）CF 2 CF 2 N（O）CF 3与反式-[IrCl（CO）L 2 ]（L = PPh 3，AsPh 3或PMePh 2），反式-[Ir ON（CF 3）2 }（CO）（PPh 3）2 ]和[Pt（PPh 3）4 ]形成七元环金属环配合物[[图略] Cl（CO）L 2 ]，[[图片省略] ON（CF 3）2 }（CO）（PPh 3）2]和[[省略图示]（PPh 3）2 ]。
• Arfaei, Ahmad; Smith, Sydney, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1791 - 1794
  作者：Arfaei, Ahmad、Smith, Sydney

  DOI：——

  日期：——
• The reaction of perfluoro-2,5-diazahexane 2,5-dioxyl with alkenes
  作者：Michael J. Green、Anthony E. Tipping

  DOI：10.1016/s0022-1139(00)80482-0

  日期：1993.11

  The liquid-phase reaction at room temperature of the title dioxyl (1) with an excess of the alkenes CH2=CHR (R=H, F, COCl), CF2=CHF, CHCl=CCl2 and cis-CHCl=CHCl gives 1:1 copolymers 3 in high yield, although with the alkenes CH2=CH2, CH2=CHF and CF2=CHF cyclic 1:1 adducts 2 are also formed in low yield. The reactions with the alkenes CH2=CMe(2), CH2=CHEt, CH2=CHCO2H and cis-HO2CCH=CHCO2H produce copolymers which are not 1:1 copolymers. The 1:1 copolymer 3f from acryloyl chloride is hydrolysed readily by water to the acrylic acid/dioxyl 1 1:1 copolymer 3j. Gas-phase reaction at room temperature of 1 with an excess of the alkenes CH2=CHR (R=Cl, Br, COCl, COF), CH2=CXCH(3) (X=Cl, Br), CHCl=CCl2, cis- and trans-CHCl=CHCl, CH2=CCl2, CF2=CCl2, CF2=CFCl and CF2=CFBr affords cyclic 1:1 adducts 2 (11.5-78%) and copolymers 3 (18.5-76.5%): hydrolysis of the acryloyl fluoride 1:1 adduct 2j gives the acrylic acid 1:1 adduct 2s in high yield.