benzonitrile oxide | 4906-88-1

• 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: benzonitrile oxide
• 英文别名: (Z)-benzylidene-aminooxyl
• CAS: 4906-88-1；135339-81-0
• 化学式: C₇H₆NO
• 分子量: 120.131
• InChiKey: RWIXSTGLOWPVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-propenyl phenyl sulfone 、 benzonitrile oxide 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以78%的产率得到(4S,5R)-4-Benzenesulfonyl-5-methyl-3-phenyl-4,5-dihydro-isoxazole
  参考文献：
  名称：

  Benedetti, Pier G. De; Quartieri, Simona; Rastelli, Augusto, Journal of the Chemical Society. Perkin transactions II, 1982, p. 95 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzaldehyde Azine Bis (N-oxide) 以 氯仿 为溶剂， 生成 benzonitrile oxide
  参考文献：
  名称：

  A Facile Preparation of Iminoxy Dimers by Hydrogen Peroxide/Peroxidase Oxidation of Aldoximes

  摘要：

  用过氧化氢/辣根过氧化物酶系统氧化 R-C6H4-CH=NOH 型苯甲醛肟（R = H、Me、OMe、Cl），可以高产率地得到相应的亚氨基氧自由基二聚体（苯甲醛偶氮）。

  DOI：

  10.1055/s-1991-26433

文献信息

• Forrester, Alexander R.; Sadd, John S., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1273 - 1278
  作者：Forrester, Alexander R.、Sadd, John S.

  DOI：——

  日期：——
• Stereochemistry of iminoxy radicals
  作者：Angelo Alberti、Gaetano Barbaro、Arturo Battaglia、Maurizio Guerra、Fernando Bernardi、Alessandro Dondoni、Gian Franco Pedulli

  DOI：10.1021/jo00317a018

  日期：1981.2
• Geometrical Isomerization and Restricted Rotation in Iminoxyl Radicals from Benzaldoximes
  作者：Marco Lucarini、Gian Franco Pedulli、Angelo Alberti

  DOI：10.1021/jo00087a009

  日期：1994.4

  The E geometrical isomers of benzaldoxime, p-chlorobenzaldoxime, and p-methylbenzaldoxime have been oxidized to the corresponding iminoxyl radicals within the cavity of an EPR spectrometer by using photolytically produced tert-butoxy radicals. The observed iminoxyls retain the same geometry (E) of the starting oximes at low temperature (ca. 190 K), while at room temperature they are almost completely converted to the more stable Z isomers. At an intermediate temperature (233 K), where both isomeric species were simultaneously detected, the rate of geometrical isomerization could be determined as 18 +/- 6 s(-1) for the radical from p-chlorobenzaldoxime. The estimated energy barrier (ca. 12 kcal mol(-1)) is much lower than that calculated in the parent oximino compounds (ca. 60 kcal mol(-1)). A rationalization of this effect in terms of Molecular Orbital theory is given. In the Z isomers of the examined iminoxyls, selective broadening of the EPR lines due to restricted rotation of the aryl ring was observed in the temperature range from 250 to 330 K. An analysis of the line shape variations with temperature performed on iminoxyl 5 provided a value of the rotational barrier of 6.18 kcal mol(-1).
• A Facile Preparation of Iminoxy Dimers by Hydrogen Peroxide/Peroxidase Oxidation of Aldoximes
  作者：Koushi Fukunishi、Kazuhiro Kitada、Ikuo Naito

  DOI：10.1055/s-1991-26433

  日期：——

  The oxidation of benzaldehyde oximes of the type R-C6H4-CH=NOH (R = H, Me, OMe, Cl) by a hydrogen peroxide/horseradish peroxidase system yields the corresponding dimers of iminoxy radicals (benzaldehyde azines) in high yields.

  用过氧化氢/辣根过氧化物酶系统氧化 R-C6H4-CH=NOH 型苯甲醛肟（R = H、Me、OMe、Cl），可以高产率地得到相应的亚氨基氧自由基二聚体（苯甲醛偶氮）。
• Benedetti, Pier G. De; Quartieri, Simona; Rastelli, Augusto, Journal of the Chemical Society. Perkin transactions II, 1982, p. 95 - 100
  作者：Benedetti, Pier G. De、Quartieri, Simona、Rastelli, Augusto、Amici, Marco De、Micheli, Carlo De、et al.

  DOI：——

  日期：——