2-[2-(2-methylphenyl)hydrazono]malononitrile | 55653-08-2

• 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-[2-(2-methylphenyl)hydrazono]malononitrile
• 英文别名: 2-Tolyl-hydrazonomalononitrile；2-[(2-methylphenyl)hydrazinylidene]propanedinitrile
• CAS: 55653-08-2
• 化学式: C₁₀H₈N₄
• mdl: MFCD01007088
• 分子量: 184.2
• InChiKey: GARUNYYLNCCBTO-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  298.7±33.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methylphenyl)hydrazono]malononitrile 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-amino-5-methyl-3-o-tolylazo-6H-pyrazolo[1,5-a]pyrimidin-7-one
  参考文献：
  名称：

  Sofan; El-Taweel; Abu El-Maati, Pharmazie, 1994, vol. 49, # 7, p. 482 - 486

  摘要：

  DOI：
• 作为产物：
  描述：

  o-toluene-diazonium chloride 、 丙二腈 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到2-[2-(2-methylphenyl)hydrazono]malononitrile
  参考文献：
  名称：

  On the Chemistry of Cinnoline I. Synthesis and Reactions of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones

  摘要：

  The synthesis of a series of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones from aryl-hydrazonomalononitrile in a one step procedure is reported. The (4-amino-cinnolin-3-yl)-p-tolyl- methanones could be annelated to the corresponding 1,2-dihydro-4-(p-tolyl)-2-oxopyrido[3,2-c]cinnoline derivatives via (4-acetamido-cinnolin-3-yl)-p-tolyl-methanones. Treatment of 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-one with POCl3 and P2S5 gave 2-chloro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. and 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-thione. Treatment of the ketone with malononitrile afforded 2-amino-3-cyano-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. Using these ketones, a facile and convenient route towards substituted pyrimidino[5,4-c]-cinnolines was developed. Chemical and spectroscopic evidences for the structures of the new compounds are presented.

  DOI：

  10.1007/pl00010201

文献信息

• Synthesis of arylhydrazone-based molecular switches using aryldiazonium silica sulfate nanocomposites and analysis of their isomerization
  作者：Amin Zarei、Leila Khazdooz、Solmaz Soltani、Alireza Najafi Chermahini、Hamidreza Aghaei、Alireza Abbaspourrad

  DOI：10.1016/j.dyepig.2021.109544

  日期：2021.10

  each synthesized compound in these two solvents. By changing the solvent from CHCl3 to DMSO, the E/Z ratios decreased. The results demonstrated that the ΔG° values for the formation of Z isomers were more negative than those of the E isomers in DMSO. This is why Z isomers are more stable than E isomers in DMSO. The results of density functional theory (DFT) calculations at B3LYP/6–311++G (d,p) level

  报道了一种通过芳基重氮硅硫酸盐纳米复合材料与丙二腈、乙酰乙酸乙酯和二甲酮反应来合成一系列芳基腙的快速有效方法。所有反应均在室温下在水中进行，相应的产物以 77-87% 的产率获得。使用乙酰乙酸乙酯合成的芳基腙中存在两种分子内氢键，使这些化合物能够通过围绕腙C N 键旋转而转换，从而导致它们的E和Z构型之间的可逆异构化。这种转换可以通过改变溶剂的极性来控制。在 CHCl 3 中研究了每种合成化合物的E/Z比和二甲基亚砜。E/Z的比率是使用1 H NMR 数据在 CDCl 3和 DMSO- d 6中计算的，并用于计算每种合成化合物在这两种溶剂中的EZ异构化的ΔG ° 。通过将溶剂从 CHCl 3改为 DMSO，E/Z比降低。结果表明，在 DMSO 中形成Z异构体的 Δ G ° 值比E异构体的更负。这就是为什么Z异构体比E更稳定DMSO 中的异构体。B3LYP/6–311++G (d,p) 理论水平的密度泛函理论
• Pyrazole compounds
  申请人：——

  公开号：US20030060453A1

  公开（公告）日：2003-03-27

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  提供药物组合物和化合物。发明的化合物显示出抗增殖活性，并且可能促进缺乏正常细胞周期和死亡调控的细胞的凋亡。发明的一个实施例提供了化合物与生理可接受载体组合的药物组合物。该药物组合物可用于治疗过度增殖障碍，包括肿瘤生长、淋巴增殖性疾病、血管生成。发明的化合物是取代吡唑和吡唑啉。
• Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics
  作者：Aykut Demirçalı

  DOI：10.1016/j.molstruc.2021.129960

  日期：2021.5

  A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised

  在0〜5℃下，将一系列重氮化的苯胺和苯胺衍生物与丙二腈在吡啶中的溶液反应，得到1a-1m的化合物。然后通过将芳基偶氮丙二腈化合物与肼偶合来合成4-芳基偶氮-3，5-二氨基-1H-吡唑（2a-2m）衍生物。最后，将合成的吡唑衍生物2a-2m化合物再次重氮化。通过使这些重氮化的化合物与3-氨基-5-羟基-1-苯基吡唑反应，得到了新的13种杂环二偶氮染料（3a-3m）加入了染料文献和染料行业。这些新合成的化合物的结构通过元素分析和光谱方法进行表征，例如傅立叶变换红外光谱-原子吸收全反射率（FT-IR-ATR），1 H-核磁共振（1 H NMR）光谱和质谱。然后研究了在二甲基亚砜，二甲基甲酰胺，乙腈，乙酸，甲醇和氯仿中的溶剂变色性质和溶剂作用。此外，研究了有机和无机酸和碱对化合物吸收光谱的影响以及苯环键合基团的取代作用。
• Mechanically Activated Solid-State Synthesis of Phenylhydrazone Derivatives via High-Speed Ball Milling
  作者：Xingyi Zhu、Yuanyuan Chen、Yuhe Chen、Jue Wang、Weike Su

  DOI：10.2174/1570178611999140404111411

  日期：2014.6

  A series of phenylhydrazone derivatives was synthesized from arenediazonium tetrafluoroborates and active methylene compounds under high-speed ball milling. The reaction occurred in the absence of the solvent and products were obtained in good yield within short reaction times (no more than 30 min).

  在高速球磨条件下，由四氟硼酸壬二唑鎓盐和活性亚甲基化合物合成了一系列苯hydr衍生物。该反应在不存在溶剂的情况下发生，并且在短反应时间内（不超过30分钟）以良好的产率获得了产物。
• Immugenic compositions and diagnostic and therapeutic uses thereof
  申请人：Zhang Zaihui

  公开号：US20050272709A1

  公开（公告）日：2005-12-08

  Pharmaceutical compositions and compounds are provided. The compounds of the invention deomonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  本发明提供了制药组合物和化合物。本发明的化合物表现出抗增殖活性，并可能促进缺乏正常细胞周期和死亡调节的细胞凋亡。在本发明的一种实施例中，提供了化合物与生理可接受载体的制药组合物。这些制药组合物可用于治疗高增殖性疾病，包括肿瘤生长、淋巴增殖性疾病、血管生成等疾病。本发明的化合物是取代的吡唑和吡唑啉。