[(e)-(4-Methoxyphenyl)diazenyl]propanedinitrile | 5436-32-8

• 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: [(e)-(4-Methoxyphenyl)diazenyl]propanedinitrile
• 英文别名: 2-[(4-methoxyphenyl)diazenyl]propanedinitrile
• CAS: 5436-32-8
• 化学式: C₁₀H₈N₄O
• 分子量: 200.2
• InChiKey: YZCHGZIONBCGFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(e)-(4-Methoxyphenyl)diazenyl]propanedinitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到3,5-diamino-4-(p-methoxyphenylazo)pyrazole
  参考文献：
  名称：

  Elfahham, Hassan Attia; Elgemeie, Galan Eldin Hamza; Ibraheim, Yusria Rizk, Liebigs Annalen der Chemie, 1988, p. 819 - 822

  摘要：

  DOI：
• 作为产物：
  描述：

  甲氧苯胺 、 丙二腈 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 反应 1.5h， 以82%的产率得到[(e)-(4-Methoxyphenyl)diazenyl]propanedinitrile
  参考文献：
  名称：

  Pyridazine derivatives and related compounds. 23*. Synthesis of 3-substituted pyrazolo[3,4-c]pyridazines and their application as disperse dyes

  摘要：

  Acetylacetone and malononitrile were coupled with diazotized arylamines to give arylazoacetyl-acetones and arylazomalononitriles. When refluxed with 3-hydrazino-4,5-diphenyl-1H-pyrazolo-[3,4-c]pyridazine in the presence of ethanol/HCl, they yielded the corresponding 3-[4-(arylazo)-3,5-di-methylpyrazol-1-yl]- and 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyri-dazine dyes. The dyes were applied to polyester and polyamide fabrics, and their spectral and fastness properties were measured.

  DOI：

  10.1007/s10593-010-0494-1

文献信息

• Syntheses of some novel imidazolidinethiones and condensed imidazoles containing arylazo moieties starting from cyanothioformamides
  作者：Ahmed M. Sh. El-Sharief、Mohamed S. A. El-Gaby、Ahmed A. Atalla、Abu-Bakr A. A. M. El-Adasy

  DOI：10.1002/hc.20113

  日期：——

  Cyclocondensation of cyanothioformamides (1) with arylhydrazonomalononitriles (2) afforded the novel imidazole derivatives (4a–e) in good yields. Isothiocyanatoazobenzene (6) was allowed to react with potassium cyanide and gave the new cyanothioformamide (7) which was reacted with 4-chlorophenyl isocyanate to yield imidazolidinethione (8). Compound (8) was subjected to react with hydrochloric acid

  氰基硫代甲酰胺 (1) 与芳基腙丙二腈 (2) 的环缩合反应以良好的收率提供了新型咪唑衍生物 (4a-e)。使异硫氰酸根合偶氮苯 (6) 与氰化钾反应，得到新的氰硫代甲酰胺 (7)，再与 4-氯苯基异氰酸酯反应得到咪唑烷硫酮 (8)。化合物(8)分别与盐酸、邻苯二胺、4-甲基苯胺和硫化氢反应，得到化合物(10)、(11)、(12)和(15)。此外，还研究了乙内酰脲 (15) 对某些亲电子试剂（如 N,N-二甲基甲酰胺-二甲基乙缩醛和亚芳基-丙二腈）的反应性。合成化合物的结构是通过分析和光谱数据确定的。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:218–225, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20113
• Wrubel, Juergen; Mayer, Roland, Zeitschrift fur Chemie, 1984, vol. 24, # 7, p. 256 - 257
  作者：Wrubel, Juergen、Mayer, Roland

  DOI：——

  日期：——
• Synthesis, Theoretical Study, and Antimicrobial Activity of Novel Polysubstituted Thiazoles
  作者：Nadia Hanafy Metwally、Sabry El-Taher

  DOI：10.3987/com-11-12141

  日期：——

  New 5-(9H-Fluoren-9-ylidene)- and 5-(1H-indan-1-ylidene)-2-thioxo-4-thiazolidinones 3a,b were synthesized Eco-friendly under microwave irradiation (MWI). These compounds undergo alkaline hydrolysis to afford the corresponding thiol derivatives 4a,b, which cyclized into polysubstituted thiazoles 6a-h using arylazomalononitriles 5a-d as nucleophilic agents. Some selected products were tested for their antimicrobial activities. The equilibrium geometries of the studied compounds were calculated at the B3LYP/6-31G(d) level of the density functional theory (DFT). Conformational analysis has been carried out to determine the most stable conformers. The relative stability of the azo and hydrazo tautomers has been investigated. The HOMO-LUMO energy gap is used in rationalizing the reactivity of the studied compounds.