3,5-吡啶二甲酸二酰肼 | 15420-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3,5-吡啶二甲酸二酰肼
• 英文名称: pyridine-3,5-dicarbohydrazide
• 英文别名: pyridine-3,5-dicarboxylic acid dihydrazide
• CAS: 15420-53-8
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: BSXGNABNXBZDAE-UHFFFAOYSA-N

物化性质

• 熔点：
  172-175 °C (decomp)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3,5-吡啶二甲酸二酰肼 在 盐酸 、 sodium nitrite 作用下， 生成 pyridine-3,5-dicarbonyl diazide
  参考文献：
  名称：

  2,3,5,6‐Tetraaminopyridine Tetracarbamate from Dinicotinic Acid

  摘要：

  The tetraethylcarbamate of 2,3,5,6-tetraaminopyridine was synthesized using dinicotinic acid as starting material in 10 steps with 23% overall yield.

  DOI：

  10.1080/00397910701865942
• 作为产物：
  描述：

  二甲基吡啶-3,5-二羧酸 在 一水合肼 作用下， 反应 24.0h， 以68.9%的产率得到3,5-吡啶二甲酸二酰肼
  参考文献：
  名称：

  一种测定苦味酸的新型酰基腙锌配位聚合物

  摘要：

  基于实际应用，设计具有新型结构的配位聚合物一直是相关研究领域的热点。报道了一种锌配位聚合物，可用作荧光探针以高选择性和灵敏度（K SV  = 17,686 M -1）检测苦味酸。其一维之字形结构具有优异的稳定性，可用于检测含有大量水的体系中的苦味酸。此外，作为固体荧光探针，经过简单洗涤后可重复用于苦味酸的检测，5个循环后检测效果不下降。我们的实验结果表明它具有作为检测苦味酸的荧光传感器的能力。

  DOI：

  10.1016/j.jssc.2022.123234

文献信息

• New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole–pyridine and 1,3,4-oxadiazole–pyrimidine hybrids
  作者：Changsheng Wang、Gun-Young Jung、Andrei S. Batsanov、Martin R. Bryce、Michael C. Petty

  DOI：10.1039/b106907c

  日期：2002.1.24

  We describe the synthesis of three new isomeric 1,3,4-oxadiazole–pyridine hybrids, namely: 2,6-, 3,5- and 2,4-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]pyridine, (PDPy-2,6, PDPy-3,5 and PDPy-2,4, respectively) and a 1,3,4-oxadiazole–pyrimidine hybrid, namely: 2,5-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]pyrimidine (PDPmDP). The X-ray crystal structures are reported for PDPy-2,4 and the known phenylene analogue 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]benzene (OXD-7) as a 1∶1 toluene solvate. The packing motif for molecules of both PDPy-2,4 and OXD-7 is that of discrete layers with the mean planes of all the molecules in the crystals parallel to within 6°. We have fabricated light-emitting diodes (LEDs) using poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV) doped with rubrene as the emissive material, with and without a thermally evaporated electron conducting/hole-blocking (ECHB) layer of PDPy-2,6, PDPy-3,5 and PDPy-2,4, PDPmDP and OXD-7, in the device configuration ITO/MEH-PPV(Ru)/ECHB layer/Al. Electroluminescence spectra indicate that light is emitted only from the MEH-PPV layer. The bilayer LEDs are considerably more efficient than single layer devices, e.g. the external quantum efficiences of devices incorporating PDPy-2,6, PDPy-3,5 and OXD-7 are 0.14, 0.04 and 0.06% at 40 mA m−2, respectively, cf. 0.007% for the reference single-layer MEH-PPV(Ru) device. There is no clear correlation between experimental EQE values and the PM3 calculated LUMO levels of the materials.

  我们描述了三种新的同分异构体1,3,4-恶二嗪-吡啶杂化物的合成，分别为：2,6-、3,5-和2,4-双[2-(4-叔丁基苯基)-1,3,4-恶二嗪-5-基]吡啶（PDPy-2,6、PDPy-3,5和PDPy-2,4）以及一种1,3,4-恶二嗪-嘧啶杂化物，即：2,5-双[2-(4-叔丁基苯基)-1,3,4-恶二嗪-5-基]嘧啶（PDPmDP）。我们报告了PDPy-2,4的X射线晶体结构，以及已知的苯基类似物1,3-双[2-(4-叔丁基苯基)-1,3,4-恶二嗪-5-基]苯（OXD-7），作为1:1的甲苯溶剂合物。PDPy-2,4和OXD-7的分子堆积模式为离散层，所有分子的平均平面在晶体内的平行度在6°以内。我们采用掺锂的聚[2-甲氧基-5-(2-乙基己基氧基)-1,4-苯乙烯]（MEH-PPV）作为发光材料制造了发光二极管（LED），并在器件配置ITO/MEH-PPV(Ru)/ECHB层/Al中加入或不加入热蒸发的电子导电/孔阻挡（ECHB）层，材料包括PDPy-2,6、PDPy-3,5、PDPy-2,4、PDPmDP和OXD-7。电致发光光谱表明，光仅从MEH-PPV层发射。双层LED的效率明显高于单层器件，例如，包含PDPy-2,6、PDPy-3,5和OXD-7的器件在40 mA m⁻²下的外量子效率分别为0.14%、0.04%和0.06%，而参考的单层MEH-PPV(Ru)器件的效率为0.007%。实验得到的外量子效率（EQE）值与材料的PM3计算的LUMO能级之间没有明显的相关性。
• Barlin, Gordon B., Australian Journal of Chemistry, 1985, vol. 38, # 10, p. 1491 - 1497
  作者：Barlin, Gordon B.

  DOI：——

  日期：——
• Bis-isatin hydrazones with novel linkers: Synthesis and biological evaluation as cytotoxic agents
  作者：Hany S. Ibrahim、Sahar M. Abou-seri、Nasser S.M. Ismail、Mahmoud M. Elaasser、Mohamed H. Aly、Hatem A. Abdel-Aziz

  DOI：10.1016/j.ejmech.2015.11.047

  日期：2016.1

  Many bis-isatins and isatins with hydrazide extension were reported to have a potential anti-proliferative effects against different cancer cell lines and cancer targets. In this study, four series of bis-isatins with hydrazide linkers were synthesized. These compounds were investigated for their antitumor activity by assessing their cytotoxic potency against HepG2, MCF-7 and HCT-116 cancer cell lines. Compound 21c possessed significant cytotoxic activity against MCF-7 (IC50 = 1.84 mu M) and HCT-116 (IC50 = 331 mu M) that surpasses the activity of doxorubicin against both cell lines (MCF-7; IC50 = 2.57 mu M and HCT-116; IC50 = 3.70 mu M). Cell cycle analysis and annexin V-FITC staining of MCF-7 cells treated with 21c suggested that the cytotoxic effect of the compound could be attributed to its pro-apoptotic activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• 2,3,5,6‐Tetraaminopyridine Tetracarbamate from Dinicotinic Acid
  作者：Matthew C. Davis、David J. Irvin

  DOI：10.1080/00397910701865942

  日期：2008.3.28

  The tetraethylcarbamate of 2,3,5,6-tetraaminopyridine was synthesized using dinicotinic acid as starting material in 10 steps with 23% overall yield.
• Photolysis and Thermolysis of Pyridyl Carbonyl Azide Monolayers on Single-Crystal Platinum
  作者：Dana K. Adkinson、David C. Magri、Jason L. Pitters、Keith Griffiths、Peter R. Norton、Mark S. Workentin

  DOI：10.1111/php.12086

  日期：2013.9

  AbstractThe photochemical and thermal reactivity of a number of acyl azide‐substituted pyridine compounds, namely nicotinyl azide, isonicotinyl azide, picolinyl azide and dinicotinyl azide with investigated as saturated monolayers on a single‐crystal Pt(111) surface in an ultrahigh vacuum chamber. Multilayers of the substrates exhibited a maximum rate of desorption at 270 K, above which, stable saturated monolayers formed as characterized by reflection‐absorption infrared spectroscopy by observation of C=O and N3 bands at 1700 cm−1, and 2100 and 1300 cm−1 respectively. The monolayers were stable up to 400 K. Photolysis of the monolayer (or heating above 400 K) results in the formation of the respective isocyanate intermediate after loss of nitrogen as evidenced by the appearance of a new infrared band at 2260 cm−1 with concomitant loss of the azide bands. The resulting isocyanate saturated monolayer is stable in absence of nucleophiles, but can be quenched with appropriate nucleophiles.