2-Trifluoromethyl-benzonitrile N-oxide | 156810-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Trifluoromethyl-benzonitrile N-oxide
• CAS: 156810-88-7
• 化学式: C₈H₄F₃NO
• 分子量: 187.121
• InChiKey: KJVWVTJHUDVAAH-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.42
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-Trifluoromethyl-benzonitrile N-oxide 在 四氢呋喃 、 dirhodium(II) tetrakis(perfluorobutyrate) 、 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 tert-butyl 3-oxo-1-(2-(trifluoromethyl)phenyl)-2-oxa-6-azabicyclo[3.1.0]hexane-5-carboxylate
  参考文献：
  名称：

  Substrate-Dependent Divergent Outcomes from Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides: Azabicyclo[3.1.0]hexanes or 5-Arylaminofuran-2(3H)-ones

  摘要：

  Dirhodium(II)-catalyzed reactions of silyl-protected enol diazoacetates with nitrile oxides exhibit high nitrile oxide substituent dependence in the production rearrangement products via dipolar cycloaddition and either the Neber rearrangement or the Lossen rearrangement.

  DOI：

  10.1021/jo3006733
• 作为产物：
  描述：

  N-羟基-2-(三氟甲基)亚氨代苯甲酰氯 在 三乙胺 作用下， 生成 2-Trifluoromethyl-benzonitrile N-oxide
  参考文献：
  名称：

  A Novel Synthesis of N-Unsubstituted β-Enamino Thioesters from 3-Arylisoxazoles and 3-Aryl-5-phenylthio-2-isoxazolines

  摘要：

  一种合成N-未取代的β-烯胺硫酯，即(Z)-S-苯基3-氨基-3-芳基丙-2-烯硫酯的新方法，通过3-芳基异噁唑或3-芳基-5-苯硫基-2-异噁唑啉来实现，并且提出了该反应的可能机理。此外，还报道了一些将一种β-烯胺硫酯[(Z)-S-苯基3-氨基-3-苯基丙-2-烯硫酯]转化为N-未取代的β-烯胺酰基衍生物（β-烯胺酯、β-烯胺酰胺和β-酮酰胺）的实例。

  DOI：

  10.1055/s-0030-1258186

文献信息

• Synthesis and Fungicidal Activity of Isoxazolines Fused to 3,5-Dichloromaleimide
  作者：Marta Konopíková、Lubor Fišera、Naďa Prónayová

  DOI：10.1135/cccc19921521

  日期：——

  3-Phenyl-5-(3,5-dichlorophenyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (III, R = H) and 3-phenyl-5-(3,5-dichlorophenyl)-6a-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (IV, R = CH₃) were prepared by 1,3-dipolar cycloaddition of substituted benzonitrile oxides I to N-(3,5-dichlorophenyl)maleimide (I, R = H), or its methyl derivative II (R = CH₃). Cycloaddition to compound II (R = CH₃) proceeded regiospecifically. Reduction of IVg with NaBH₄ was regio- and stereoselective to yield the hydroxylactams VIIg, VIIIg, and IXg. Antifungal activity of several products was worse than that of commercial preparations.

  通过将取代苯甲腈氧化物I加到N-(3,5-二氯苯基)马来酰亚胺（I，R = H）或其甲基衍生物II（R = CH3）上，制备了3-苯基-5-(3,5-二氯苯基)-3a,4,6,6a-四氢吡咯并[3,4-d]异噁唑酮（III，R = H）和3-苯基-5-(3,5-二氯苯基)-6a-甲基-3a,4,6,6a-四氢吡咯并[3,4-d]异噁唑酮（IV，R = ）。与化合物II（R = ）的环加成反应是区域选择性的。用NaBH4还原IVg，区域和立体选择性地生成羟基内酰胺VIIg，VIIIg和IXg。几种产品的抗真菌活性不如商业制剂。
• Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
  作者：Leonardo Di Nunno、Paola Vitale、Antonio Scilimati

  DOI：10.1016/j.tet.2008.09.063

  日期：2008.12

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.