O-(2,4-Dinitrophenyl)-acetonoxim | 13181-10-7

• 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: O-(2,4-Dinitrophenyl)-acetonoxim
• 英文别名: O-(2,4-dinitrophenyl)acetoxime；N-(2,4-dinitrophenoxy)propan-2-imine
• CAS: 13181-10-7
• 化学式: C₉H₉N₃O₅
• 分子量: 239.188
• InChiKey: FRNRURMYMBFWLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  O-(2,4-Dinitrophenyl)-acetonoxim 、 正丁胺 以 乙腈 为溶剂， 生成 2,4-dinitro-N-butylaniline
  参考文献：
  名称：

  Bhattacharjee, Gurudas; Singh, Ashok Kumar; Singh, Rupam, Journal of the Indian Chemical Society, 2003, vol. 80, # 2, p. 95 - 99

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-dinitrobenzene-1-diazonium tertafluoroborate 在 氢氧化钾 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 O-(2,4-Dinitrophenyl)-acetonoxim
  参考文献：
  名称：

  Formation of O,N-disubstituted hydroxylamines and ketoxime esters in reactions between triazene 1-oxides and bases

  摘要：

  A new method has been put forward for the synthesis of O,N-disubstituted hydroxylamines and ketoxime esters that is based on the reaction of triazene 1-oxides containing strong electron-withdrawing substituents with bases.

  DOI：

  10.1007/bf00863828

文献信息

• The ultraviolet spectra of O-(2,4-dinitrophenyl)oximes and 2,4-dinitrophenylhydrazones: transmission of electronic effects through O and NH groups
  作者：Zvi Rappoport、Tuvia Sheradsky

  DOI：10.1039/j29670000898

  日期：——

  The λmax values in the ultraviolet spectra of 61 pairs of 2,4-dinitrophenylhydrazones (DNP) and O-(2,4-dinitrophenyl)oximes (DNO) were compared. The λmax(DNP)–λmax(DNO)=Δλ values are 61 ± 1 mµ for aliphatic carbonyl compounds, 69 ± 1 mµ for aromatic aldehydes and ketones, and 71 ± 1 mµ for diaryl ketones. Deviations were found for several ortho substituents or for para substituents having strong +M

  比较了61对2,4-二硝基苯基hydr（DNP）和O-（2,4-二硝基苯基）肟（DNO）在紫外光谱中的λmax值。的λ最大（DNP）-λ最大值（DNO）=Δλ的值是61±1米μ为脂族羰基化合物，69±1米μ为芳香醛和酮，和71±1米μ为二芳基酮。被发现的数偏差邻取代基或对位具有强+取代基中号效果。讨论了确定恒定性和Δλ值偏差的因素。
• Experimental evidence of chalcogen bonding at oxygen
  作者：Thomas Fellowes、Benjamin L. Harris、Jonathan M. White

  DOI：10.1039/c9cc09896h

  日期：——

  which exhibited characteristics consistent with a chalcogen bond. The O-N bond length of the oxime was appreciably longer than the expected value, and NBO calculations indicated the presence of a n(O) → σ(O-N) orbital delocalisation. Topological analysis of the experimental electron density of two analogues shows the presence of a bond path between the two oxygen atoms, with ρ(r) and ∇2ρ(r) values consistent

  观察到邻-硝基-O-芳基肟表现出短的OO接触，其表现出与硫属元素键一致的特性。肟的ON键长度明显长于预期值，NBO计算表明存在（O）→σ（ON）轨道离域。两种类似物的实验电子密度的拓扑分析表明，两个氧原子之间存在键合路径，其中ρ（r）和∇2ρ（r）的值与静电相互作用一致。最后，静电势的计算表明存在一个σ孔，“吸烟枪”表明存在CH键。这些结果是不寻常的，因为通常不认为氧气是Ch键供体，尤其是在未活化的系统（例如肟）中。
• Synthesis of diaziridines from oxime esters
  作者：N. N. Makhova、V. Yu. Petukhova、L. I. Khmel'nitskii

  DOI：10.1007/bf00952389

  日期：1982.9
• Reaction of aryldiazonium salts with acetone oxime
  作者：S. G. Zlotin、O. V. Prokshits、O. A. Luk'yanov

  DOI：10.1007/bf00864353

  日期：1992.8

  The reaction of aryl diazonium salts containing electron-withdrawing substituents in the aromatic ring with acetone oxime leads to the formation of nitrogen-containing products instead of the expected functional derivatives of 1-alkyl-3-aryltriazene 1-oxides. The structure of these products is a function of the number and chemical nature of the substituents in the diazo component.
• Werner, Chemische Berichte, 1894, vol. 27, p. 1656
  作者：Werner

  DOI：——

  日期：——