2-(4-nitro-phenylhydrazono)-3-oxo-butyronitrile | 28317-67-1

• 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: 2-(4-nitro-phenylhydrazono)-3-oxo-butyronitrile
• 英文别名: N-(4-nitroanilino)-2-oxopropanimidoyl cyanide
• CAS: 28317-67-1
• 化学式: C₁₀H₈N₄O₃
• 分子量: 232.199
• InChiKey: FQHKOKBFYBCHAX-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±44.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-nitro-phenylhydrazono)-3-oxo-butyronitrile 以 乙腈 为溶剂， 反应 0.17h， 生成 乙烯酮
  参考文献：
  名称：

  Gas-phase kinetics of elimination reactions of pentane-2,4-dione derivatives. Part ii [1]. Thermolysis of derivatives and analogues of 3-phenylhydrazonopentane-2,4-dione

  摘要：

  Six analogues and derivatives (1-6) of 3-phenylhydrazonopentane-2.4-dione (7) were subjected to gas-phase thermolysis. The Arrhenius log A (s(-1)) and Ea (kJ mol(-1)) of the analogues (1-5) are, respectively: 10.42 and 140.8 for 1-cyano-1-phenyl-hydrazonopropanone (1), 11.19 and 135.4 for 1-cyano-1-(p-nitrophenylhydrazono)-propanone (2), 10.68 and 144.9 for l-cyano-1-(p-methoxyphenylhydrazono)propanone (3), 11.76 and 137.8 for 1-cyano-3-phenyl-1-phenylhydrazonopropanone (4), and 11.29 and 145.9 for 1-cyano-1-phenylhydrazonobutanone (5). The corresponding values for ethyl 3-oxo-2-phenylhydrazonobutanoate (6) are 11.90 s(-1) and 141.3 kJ mol(-1). The rates of reaction at 600 K are compared with those of the title diketone (7) and of pentane-2,4-dione (8) and rationalized in terms of a plausible elimination pathway involving a semiconcerted six-membered transition state. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:7<457::aid-kin1>3.0.co;2-r
• 作为产物：
  描述：

  potassium cyanide 、 N-(4-硝基苯基)-2-氧代丙烷腙酰氯 以 乙醇 为溶剂， 生成 2-(4-nitro-phenylhydrazono)-3-oxo-butyronitrile
  参考文献：
  名称：

  Synthesis and Tautomeric Structure of 3,7-bis(arylazo)-2,6-dimethyl-1H-imidazo[1,2-b]pyrazoles

  摘要：

  从 N-芳基-2-氧代丙烷肼酰氯开始，制备了三个系列的 3,7-双（芳基偶氮）-2,6-二甲基-1 H-咪唑并[1,2-b]吡唑。测定了酸解离常数 p Ka，并将其与哈米特方程联系起来。这种关联的结果以及光谱数据表明，标题化合物主要以 1 H-双（芳基偶氮）形式存在。

  DOI：

  10.3184/174751913x13588723344455

文献信息

• An Unusual Rearrangement of Pyrazole Nitrene and Coarctate Ring-Opening/Recyclization Cascade: Formal CH–Acetoxylation and Azide/Amine Conversion without External Oxidants and Reductants
  作者：Elena Chugunova、Almir S. Gazizov、Daut Islamov、Victoria Matveeva、Alexander Burilov、Nurgali Akylbekov、Alexey Dobrynin、Rakhmetulla Zhapparbergenov、Nurbol Appazov、Beauty K. Chabuka、Kimberley Christopher、Daria I. Tonkoglazova、Igor V. Alabugin

  DOI：10.3390/molecules28217335

  日期：——

  of a nitrene moiety initiates a sequence of steps leading to remote oxidative C–H functionalization (R–CH3 to R–CH2OC(O)R’) and the concomitant reduction of the nitrene into an amino group. No external oxidants or reductants are needed for this formal molecular comproportionation. Detected and isolated intermediates and computational analysis suggest that the process occurs with pyrazole ring opening

  我们报告了一种不寻常的转变，其中氮宾部分的瞬时形成启动了一系列步骤，导致远程氧化C–H功能化（R–CH3到R–CH2OC(O)R'），并同时将氮宾还原成氨基团体。这种正式的分子复合反应不需要外部氧化剂或还原剂。检测和分离的中间体以及计算分析表明该过程发生在吡唑开环和再循环过程中。
• Essential iris atrophy mimicking iris neoplasm: an ultrasound biomicroscopic study
  作者：Hesham M. Lakosha、Charles J. Pavlin、E. Rand Simpson

  DOI：10.1016/s0008-4182(00)80127-1

  日期：2000.12
• Gas-phase kinetics of elimination reactions of pentane-2,4-dione derivatives. Part ii [1]. Thermolysis of derivatives and analogues of 3-phenylhydrazonopentane-2,4-dione
  作者：Nouria A. Al-Awadi、Mohamed H. Elnagdi、Hanan A. Al-Awadhi、Osman M. E. El-Dusouqui

  DOI：10.1002/(sici)1097-4601(1998)30:7<457::aid-kin1>3.0.co;2-r

  日期：——

  Six analogues and derivatives (1-6) of 3-phenylhydrazonopentane-2.4-dione (7) were subjected to gas-phase thermolysis. The Arrhenius log A (s(-1)) and Ea (kJ mol(-1)) of the analogues (1-5) are, respectively: 10.42 and 140.8 for 1-cyano-1-phenyl-hydrazonopropanone (1), 11.19 and 135.4 for 1-cyano-1-(p-nitrophenylhydrazono)-propanone (2), 10.68 and 144.9 for l-cyano-1-(p-methoxyphenylhydrazono)propanone (3), 11.76 and 137.8 for 1-cyano-3-phenyl-1-phenylhydrazonopropanone (4), and 11.29 and 145.9 for 1-cyano-1-phenylhydrazonobutanone (5). The corresponding values for ethyl 3-oxo-2-phenylhydrazonobutanoate (6) are 11.90 s(-1) and 141.3 kJ mol(-1). The rates of reaction at 600 K are compared with those of the title diketone (7) and of pentane-2,4-dione (8) and rationalized in terms of a plausible elimination pathway involving a semiconcerted six-membered transition state. (C) 1998 John Wiley & Sons, Inc.
• Synthesis and Tautomeric Structure of 3,7-bis(arylazo)-2,6-dimethyl-1<i>H</i>-imidazo[1,2-<i>b</i>]pyrazoles
  作者：Ahmad Sami Shawali、Magda A. Abdallah、Mohamed R. Shehata、Mohamed Kandil

  DOI：10.3184/174751913x13588723344455

  日期：2013.3

  Three series of 3,7-bis(arylazo)-2,6-dimethyl-1 H-imidazo[1,2- b]pyrazoles were prepared starting from N-aryl-2-oxo-propanehydrazonoyl chlorides. The acid dissociation constants p Ka were determined and correlated with the Hammett equation. The results of such correlations together with the spectroscopic data indicated that the title compounds exist predominantly in the 1 H-bis(arylazo) form.

  从 N-芳基-2-氧代丙烷肼酰氯开始，制备了三个系列的 3,7-双（芳基偶氮）-2,6-二甲基-1 H-咪唑并[1,2-b]吡唑。测定了酸解离常数 p Ka，并将其与哈米特方程联系起来。这种关联的结果以及光谱数据表明，标题化合物主要以 1 H-双（芳基偶氮）形式存在。