phenylazo acetylacetonitrile | 28317-57-9

• 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: phenylazo acetylacetonitrile
• 英文别名: 3-oxo-2-phenylhydrazono-butyronitrile；β-Oxo-α-phenylhydrazono-buttersaeure-nitril；N-anilino-2-oxopropanimidoyl cyanide
• CAS: 28317-57-9
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: OHHMFUWOGBCGKS-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  306.9±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 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：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenylazo acetylacetonitrile 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：

  5-甲基异恶唑 在 乙醚 、 sodium ethanolate 作用下， 生成 phenylazo acetylacetonitrile
  参考文献：
  名称：

  Claisen, Chemische Berichte, 1909, vol. 42, p. 67

  摘要：

  DOI：

文献信息

• 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。
• Novel Synthesis of 4-Bromo-3-oxo-2-phenylhydrazonobutyronitrile and 4-Cyano-3-oxo-2-phenylhydrazonobutyronitrile: Synthesis of Pyridazine, Thiazole, 1,2,4-Triazine and Pyrido[2,3-e]-1,2,4-triazine Derivatives
  作者：Rafat Milad Mohareb、Nadia Iskander Abdel-Sayed

  DOI：10.1135/cccc19921758

  日期：——

  4-Bromo-3-oxo-2-phenylhydrazono-butyronitrile (II) reacted with thioamides to afford the thiazole derivatives III and VI. Compound II reacted with nucleophilic reagents to afford XIIIa and XIIIb. The reactivity of XIIIa with some chemical reagents was studied to afford pyridazine, thiazole, 1,2,4-triazine derivatives.

  4-溴-3-氧代-2-苯基肼基-丁腈（II）与硫代胺反应，形成噻唑衍生物III和VI。化合物II与亲核试剂反应，形成XIIIa和XIIIb。研究了XIIIa与一些化学试剂的反应性，形成吡啶嗪、噻唑、1,2,4-三嗪衍生物。
• Elnagdi, Mohamed Hilmy; Elghandour, Ahmed Hafez Hussien; Harb, Abdel Fattah Ali, Heterocycles, 1994, vol. 38, # 4, p. 739 - 750
  作者：Elnagdi, Mohamed Hilmy、Elghandour, Ahmed Hafez Hussien、Harb, Abdel Fattah Ali、Hussien, Abdel Haleem Mostafa、Metwally, Saoud Abdel Meniem

  DOI：——

  日期：——
• Ghozlan, Said Ahmed Soliman; Mohamed, Mona Hassan; Soliman, Ahmed Yousef, Gazzetta Chimica Italiana, 1989, vol. 119, # 2, p. 95 - 98
  作者：Ghozlan, Said Ahmed Soliman、Mohamed, Mona Hassan、Soliman, Ahmed Yousef、Bakeer, Hadir

  DOI：——

  日期：——
• El-Kousy; Mohareb; Riad, Pakistan Journal of Scientific and Industrial Research, 1998, vol. 41, # 2, p. 81 - 85
  作者：El-Kousy、Mohareb、Riad、Elnagdi

  DOI：——

  日期：——