3,4-bis(3-nitrophenyl)furoxan | 51003-63-5

• 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: 3,4-bis(3-nitrophenyl)furoxan
• 英文别名: Di-m-nitrophenylfuroxane；3,4-bis-(3-nitro-phenyl)-furazan 2-oxide；bis-(3-nitro-phenyl)-furazan-2-oxide；Bis-(3-nitro-phenyl)-furazan-2-oxid；3,4-Bis-<3-nitro-phenyl>-furoxan；3,4-Bis(3-nitrophenyl)-1,2,5-oxadiazole 2-oxide；3,4-bis(3-nitrophenyl)-2-oxido-1,2,5-oxadiazol-2-ium
• CAS: 51003-63-5
• 化学式: C₁₄H₈N₄O₆
• 分子量: 328.241
• InChiKey: ZTKFCKKIGNJNAT-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  516.7±60.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  m-nitrobenzhydroxamoyl chloride 在 乙醇 、 二甲胺 作用下， 生成 3,4-bis(3-nitrophenyl)furoxan
  参考文献：
  名称：

  Brady; Peakin, Journal of the Chemical Society, 1929, p. 2269

  摘要：

  DOI：

文献信息

• New methods of preparation of nitrile oxides and the corresponding disubstituted furoxans by interaction of N2O4 with salts of substituted dinitromethanes
  作者：N. N. Makhova、I. V. Ovchinnikov、V. G. Dubonos、Yu. A. Strelenko、L. I. Khmel'nitsky

  DOI：10.1007/bf00699994

  日期：1993.1

  A new method of generation of nitrile oxides through interaction of N2O4 with salts of substituted dinitromethanes (1) has been worked out. It has been shown by1H,13C,14N NMR spectroscopy that this reaction proceeds via dinitronitrosomethyl intermediates (one of these has been isolated), and that the reaction is feasible only for substituents capable of conjugation with the nitrile oxide fragment.

  已经研究出一种通过 N2O4 与取代二硝基甲烷 (1) 的盐相互作用生成腈氧化物的新方法。1H、13C、14N NMR光谱表明，该反应通过二亚硝基甲基中间体（其中之一已被分离）进行，并且该反应仅对于能够与氧化腈片段缀合的取代基是可行的。在所得腈氧化物环二聚化的基础上，开发了合成对称取代呋喃的制备方法。
• Syntheses based on nitrile oxides. 1. Reaction of aromatic nitrile oxides with N-cyanimides
  作者：V. A. Ogurtsov、O. A. Rakitin、N. V. Obruchnikova、L. F. Chertanova、A. A. Gazikasheva、L. I. Khmel'nitskii

  DOI：10.1007/bf00958257

  日期：1990.9

  The reaction of trialkylaminocyanimides with aromatic nitrile oxides leads to trialkylamino-(3-aryl-1,2,4-oxadiazol-5-yl)imides, while the corresponding reactions with sulfylcyanimines and phosphincyanimides do not take place. Using x-ray structural analysis the principal structural features of the 1,2,4-oxadiazole products have been elucidated.
• Ruggeri, Gazzetta Chimica Italiana, 1923, vol. 53, p. 694
  作者：Ruggeri

  DOI：——

  日期：——
• Infrared Spectra of the Nitrile N-Oxides: Some New Furoxans
  作者：RICHARD H. WILEY、B. J. WAKEFIELD

  DOI：10.1021/jo01074a014

  日期：1960.4
• Cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine: Studies in regio- and stereoselectivity
  作者：L. Fišera、F. Sauter、J. Fröhlich、Y. Feng、P. Ertl、K. Mereiter

  DOI：10.1007/bf00811848

  日期：1994.5

  A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine. Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients. X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated DELTAH(f)-values of all possible cycloadducts.