(E)-1-(4-bromobenzylidene)-2-(2,4-dinitro phenyl)hydrazine | 2087-20-9

• 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: (E)-1-(4-bromobenzylidene)-2-(2,4-dinitro phenyl)hydrazine
• 英文别名: (E)-1-(4-bromobenzylidene)-2-(2,4-dinitrophenyl)hydrazine；4-Bromobenzaldehyde, 2,4-dinitrophenylhydrazone；N-[(E)-(4-bromophenyl)methylideneamino]-2,4-dinitroaniline
• CAS: 2087-20-9
• 化学式: C₁₃H₉BrN₄O₄
• 分子量: 365.143
• InChiKey: SFVBWARTAYZWKI-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-bromobenzylidene)-2-(2,4-dinitro phenyl)hydrazine 在 sodium azide 作用下， 以 水 为溶剂， 反应 4.0h， 以78%的产率得到5-(p-bromophenyl)-N-(2,4-dinitrophenyl)-4,5-dihydro-1H-tetrazol-1-amine
  参考文献：
  名称：

  Synthesis and Characterization of Novel Five-Membered Heterocycles and Their Activity against Candida Yeasts

  摘要：

  Some new tetrazole derivatives were prepared by the reaction between the prepared azomethine compounds I-6-I-10 with sodium azide in anhydrous tetrahydrofuran (THF) with a few drops of distilled water and under reflux conditions. Azomethine compounds were prepared by thermal condensation reactions of aromatic aldehydes with primary aromatic amines. The prepared compounds (tetrazole derivatives) were screened for their antibacterial activity (by disc diffusion method). Compound I-6 is the most active derivative that has recorded a significantly (p<0.01) stronger influence to inhibit the growth of Candida zeylanoides with an average zone of inhibition of 26.0 mm. Derivatives I-7 and I-9 showed the lowest zone of inhibition of 8.0 mm against Candida zeylanoides. This study may be helpful in designing more potential anticandidal agents for therapeutic use in the future.

  DOI：

  10.17344/acsi.2018.4719
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 在 硫酸 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.69h， 生成 (E)-1-(4-bromobenzylidene)-2-(2,4-dinitro phenyl)hydrazine
  参考文献：
  名称：

  在流动中使用 DIBAL-H 有效部分还原 α,β-不饱和酯

  摘要：

  在低温条件 (–97 °C) 下，使用流动反应器系统在 1 秒内以高流速 (18 mL min-1) 部分还原 α,β-不饱和酯和苯甲酸酯衍生物以形成相应的醛。市售的氢化二异丁基铝 (DIBAL-H) 用作还原剂。除了 4-甲氧基肉桂酸酯和 4-甲氧基苯甲酸酯外，所需的烯醛和苯甲醛衍生物均以中等至高产率选择性地和经济地氧化还原。

  DOI：

  10.1002/ejoc.201402675

文献信息

• SYNTHESIS AND ANTIFUNGAL ACTIVITY OF DIARYL HYDRAZONES FROM 2,4-DINITROPHENYLHYDRAZINE
  作者：SERGIO ORTIZ、RONALD NELSON、VÍCTOR KESTERNICH、MARCIA PÉREZ-FEHRMANN、PHILIPPE CHRISTEN、LAURENCE MARCOURT

  DOI：10.4067/s0717-97072016000300015

  日期：——

  A new series of diarylhydrazones derived from 2,4-dinitrophenylhydrazine were synthesized via condensation with aromatic aldehydes whose structures have been determined by mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectra. Yields were 50-99%. All compounds were screened in vitro for their antifungal activity. Preliminary results indicated that compounds 3g and 3h exhibited promising antifungal potency. Understanding of the structure of these compounds establishes a preliminary structure-activity relationship to form the basis of further investigation.
• Hearn, Michael J.; Sy, Karen Grace, Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 339 - 342
  作者：Hearn, Michael J.、Sy, Karen Grace

  DOI：——

  日期：——
• HEARN, MICHAEL J.;SY, KAREN GRACE, BULL. SOC. CHIM. BELG., 98,(1989) N, C. 339-342
  作者：HEARN, MICHAEL J.、SY, KAREN GRACE

  DOI：——

  日期：——
• An Efficient Partial Reduction of α,β-Unsaturated Esters Using DIBAL-H in Flow
  作者：Masahito Yoshida、Hiroyuki Otaka、Takayuki Doi

  DOI：10.1002/ejoc.201402675

  日期：2014.9

  The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min–1) under cryogenic conditions (–97 °C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and

  在低温条件 (–97 °C) 下，使用流动反应器系统在 1 秒内以高流速 (18 mL min-1) 部分还原 α,β-不饱和酯和苯甲酸酯衍生物以形成相应的醛。市售的氢化二异丁基铝 (DIBAL-H) 用作还原剂。除了 4-甲氧基肉桂酸酯和 4-甲氧基苯甲酸酯外，所需的烯醛和苯甲醛衍生物均以中等至高产率选择性地和经济地氧化还原。
• Synthesis and Characterization of Novel Five-Membered Heterocycles and Their Activity against Candida Yeasts
  作者：Hiba Maher Tawfeeq、Rasim Farraj Muslim、Obaid Hasan Abid、Mustafa Nadhim Owaid

  DOI：10.17344/acsi.2018.4719

  日期：——

  Some new tetrazole derivatives were prepared by the reaction between the prepared azomethine compounds I-6-I-10 with sodium azide in anhydrous tetrahydrofuran (THF) with a few drops of distilled water and under reflux conditions. Azomethine compounds were prepared by thermal condensation reactions of aromatic aldehydes with primary aromatic amines. The prepared compounds (tetrazole derivatives) were screened for their antibacterial activity (by disc diffusion method). Compound I-6 is the most active derivative that has recorded a significantly (p<0.01) stronger influence to inhibit the growth of Candida zeylanoides with an average zone of inhibition of 26.0 mm. Derivatives I-7 and I-9 showed the lowest zone of inhibition of 8.0 mm against Candida zeylanoides. This study may be helpful in designing more potential anticandidal agents for therapeutic use in the future.