N,N-bis(trifluoromethyl)-O-acetylhydroxylamine | 22665-00-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-bis(trifluoromethyl)-O-acetylhydroxylamine
• 英文别名: N-acetoxy-bis(trifluoromethyl)-amine；acetyl bistrifluormethylnitroxide；[Bis(trifluoromethyl)amino] acetate
• CAS: 22665-00-5
• 化学式: C₄H₃F₆NO₂
• 分子量: 211.064
• InChiKey: NSFWHUGLADOJTN-UHFFFAOYSA-N

物化性质

• 沸点：
  36.2±50.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  氧代[二(三氟甲基)]铵 、 乙醛 生成 N,N-bis(trifluoromethyl)-O-acetylhydroxylamine
  参考文献：
  名称：

  一氧化氮化学。第四部分 双三氟甲基硝基氧与醛的反应

  摘要：

  三氟甲基氮氧抽象从乙醛，丙醛，新戊醛，苯甲醛，醛的氢原子米-和p -tolualdehyde，对苯二甲醛，和五氟苯甲醛非常方便，得到NN -bistrifluoromethylhydroxylamine和相应的（bistrifluoromethylamino -氧基）羰基-烷烃或-arene在几乎定量的产量。羰基化合物ArCO 2 ·N（CF 3）2（Ar = Ph或C 6 F 5）产生相应的芳烃羧酸，并且在高温下双三氟甲基硝基氧对苯基化合物的攻击导致核取代并形成（双三氟甲基氨基-氧基）[（双三氟甲基氨基-氧基）羰基]苯。

  DOI：

  10.1039/p19730000080

文献信息

• Nitroxide chemistry. Part II. Reaction of bistrifluoromethyl nitroxide with some alkanes and alkenes; free-radical dehydrogenation of alkanes to alkenes
  作者：R. E. Banks、R. N. Haszeldine、B. Justin

  DOI：10.1039/j39710002777

  日期：——

  Methane resists attack by bistrifluoromethyl nitroxide at room temperature, but hydrogen abstraction occurs with ethane [→ EtR, RCH2·CH2R, MeCOR; R =(CF3)2N·O throughout this paper], propane (→ PriR, MeCHR·-CH2R, Me2CO), isobutane (→ ButR, Me2CR·CH2R), isopentane (→ Me2CREt, Me2CR·CHRMe, RCH2·-CRMeEt), and neopentane (→ ButCH2R, ButCOR). Reaction of the nitroxide with 3-methylbut-1-ene at room temperature

  甲烷在室温下可抵抗双三氟甲基硝基氧的攻击，但乙烷会吸收氢[ → EtR，RCH 2 ·CH 2 R，MeCOR; R =（CF 3）2 N·ö贯穿本文]，丙烷（→镨我R，MeCHR·-CH 2 R，我2 CO），异丁烷（→卜吨R，我2 CR·CH 2 R），异戊烷（→ Me 2 CREt，Me 2 CR·CHRMe，RCH 2 ·-CRMeEt）和新戊烷（→ Bu t CH 2R，卜吨COR）。氮氧化物与3-甲基丁-1-烯在室温下的反应导致烯丙基叔氢的快速提取和异构丁烯Me 2 CR·CH：CH 2和Me 2 C：CH的1：1混合物的形成·CH 2 R几乎定量收率。当用双三氟甲基硝基氧处理异丁烯，2-甲基丁-1-烯，2-甲基丁-2-烯或四甲基乙烯时，加氢比提取氢更为重要。
• The synthesis of [bis(trifluoromethyl)amino-oxy]-substituted dialkyldichlorosilanes and their conversion into polysiloxanes
  作者：Graham E. Ducker、Anthony E. Tipping

  DOI：10.1016/0022-1139(93)02917-4

  日期：1994.3

  (CF3)2NOCH2CH2CH2SiMeCl2 (29) are converted into the corresponding polysiloxanes (‘prepolymers’ of low molecular weight) by reaction with reagents including water, acid, base and metal oxides; equilibration of the polysiloxane ‘prepolymer’ 38, derived from dichlorosilane 29 by heating with powdered KOH, affords a solid rubbery polysiloxane.

  羟基（CF 3）2 NO·（1）对硅烷Et 2 SiCl 2的乙基的攻击发生在相对于硅的α和β位置（比率31:45），而硅烷Pr ñ SiMeCl 2攻击发生在丙基的β位上。对于乙硅烷Me 3 SiCH 2 SiMe 3，用氧基1处理形成的主要含硅产物是Me 3 SiF，（CF 3）2 NOSiMe 3和Me 3 SiSiMe 3。斯皮尔催化（H 2 PtCl 6）将硅烷HSiCl 2 X（XMe和Cl）加到烯烃（CF 3）2 NOCH 2 CHCH 2中得到加合物（CF 3）2 NOCH 2 CH 2 CH高产率的2 SiCl 2 X（29，XMe）和（28，XCl）。取代的二氯硅烷（CF 3）2 NOCH 2 CH 2 SiEtCl 2（9），（CF 3）2通过与水，酸，碱和水等试剂反应，将NOCHMeCH 2 SiMeCl 2（14）和（CF 3）2 NOCH 2 CH 2 CH
• Preparation and reactions of mercury(<scp>II</scp>) bistrifluoromethylnitroxide
  作者：H. J. Emeléus、Jean'ne M. Shreeve、P. M. Spaziante

  DOI：10.1039/j19690000431

  日期：——

  Mercury(II) bistrifluoromethylnitroxide has been prepared by reaction of mercury with an excess of liquid bistrifluoromethylnitroxide radical. It is a white crystalline solid which dissociates to mercury and the free radical at 85°. It reacts at room temperature with typical compounds containing B–Cl, C–halogen, Si–Cl, Ge–Cl, and P–Cl bonds to give the corresponding bistrifluoromethylnitroxide derivative

  通过使汞与过量的液态三氟甲基硝基氧自由基反应制备了汞（II）型双三氟甲基硝基氧。它是白色结晶固体，在85°时会分解为汞和自由基。它在室温下与含有B–Cl，C–卤素，Si–Cl，Ge–Cl和P–Cl键的典型化合物反应，以高收率得到相应的双三氟甲基硝基氧衍生物。三（双三氟甲基硝基氧）硼与氟化铯产生1：1的加合物。
• 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
  作者：Anthony E. Tipping、Rajendraprasad B. Yadav

  DOI：10.1016/0022-1139(93)02976-l

  日期：1994.7

  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.