pyruvic acid phenylhydrazone

• 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: pyruvic acid phenylhydrazone
• 英文别名: Brenztraubensaeure-phenylhydrazon；2-(phenylhydrazinylidene)propanoic acid
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: CSTSUTMIORLRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyruvic acid phenylhydrazone 生成 乙醛苯腙
  参考文献：
  名称：

  Fischer,E.; Jourdan, Chemische Berichte, 1883, vol. 16, p. 2241

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl pyruvate phenylhydrazone 在 盐酸 作用下， 生成 pyruvic acid phenylhydrazone
  参考文献：
  名称：

  Bamberger; de Gruyter, Journal fur praktische Chemie (Leipzig 1954), 1901, vol. <2> 64, p. 239

  摘要：

  DOI：

文献信息

• Sulfamic acid as a green, reusable catalyst for stepwise, tandem &amp; one-pot solvent-free synthesis of pyrazole derivatives
  作者：Veera Swamy Konkala、Pramod Kumar Dubey

  DOI：10.1016/j.cclet.2017.02.005

  日期：2017.7

  Abstract Sulfamic acid (SA) is a bi-functional, cost-effective and reusable green catalyst for the synthesis of 4-(pyrazol-4-yl)methylenepyrazol-5(4 H )-one derivatives by one-pot, three-component condensation of pyrazol-4-carbaxaldehydes, β -ketoesters and phenyl hydrazine (Route-I). In addition to this method, another simple condensation of pyrazol-4-carbaxaldehydes with pyrazolone in the presence

  摘要氨基磺酸（SA）是一种双功能，经济高效且可重复使用的绿色催化剂，用于通过一锅，三组分合成4-（吡唑-4-基）亚甲基吡唑-5（4 H）-一衍生物。吡唑-4-氨基甲醛，β-酮酸酯和苯基肼的缩合反应（路线Ⅰ）。除此方法外，还报道了在无溶剂条件下，在SA的存在下，吡唑-4-氨基甲醛与吡唑酮的另一种简单缩合反应，收率很高。这些方案的优点是条件温和，无水后处理，收率高，催化剂容易获得，无需色谱分离和廉价的固体酸催化剂。此外，SA可以循环使用五次而不会失去其催化活性。
• Cleavage of 2-acetyl-2-phenylazopropionanilide and related compounds by boron trifluoride. New Japp–Klingemann reactions
  作者：G. C. Barrett、M. M. El-abadelah、M. K. Hargreaves

  DOI：10.1039/j39700001986

  日期：——

  2-Acetyl, 2-cyano-, and 2-nitro-2-phenylazopropionic acid derivatives suffer cleavage of the phenylazo-grouping on treatment with boron trifluoride, giving benzenediazonium tetrafluoroborate and the corresponding difluoroboron propionic acid derivative; 2-cyano- or 2-nitro-2-phenylazoisobutyronitrile and the corresponding amides behave similarly, but 1-phenylazo-2-naphthol gives a difluoroboron salt, and

  在用三氟化硼处理时，2-乙酰基，2-氰基-和2-硝基-2-苯基偶氮丙酸衍生物遭受苯基偶氮基团的裂解，得到四氟硼酸苯重氮鎓和相应的二氟硼丙酸衍生物。2-氰基或2-硝基-2-苯基偶氮异丁腈和相应的酰胺具有相似的行为，但是1-苯基偶氮-2-萘酚生成二氟硼盐，并且在处理时将2-苯基偶氮（二苯基甲基）乙酸酯环化为1,3-二苯基吲唑与三氟化硼。在尝试的酮羰基羰基缩合反应过程中，酰基-2-苯基偶氮丙酸酯的酰基丢失，并转化为相应的苯基azo；描述了扩大Japp–Klingemann反应范围的新例子。
• Quantification and Mass Isotopomer Profiling of α-Keto Acids in Central Carbon Metabolism
  作者：Michael Zimmermann、Uwe Sauer、Nicola Zamboni

  DOI：10.1021/ac500472c

  日期：2014.3.18

  Mass spectrometry has been established as a powerful and versatile technique for studying cellular metabolism. Applications range from profiling of metabolites to accurate quantification and tracing of stable isotopes through the biochemical reaction network. Despite broad coverage of central carbon metabolism, most methods fail to provide accurate assessments of the α-keto acids oxaloacetic acid, pyruvate, and glyoxylate because these compounds are highly reactive and degraded during sample processing and mass spectrometric measurement. We present a derivatization procedure to chemically stabilize these compounds readily during quenching of cellular metabolism. Stable derivatives were analyzed by ultrahigh pressure liquid chromatography coupled tandem mass spectrometry to accurately quantify the abundance of α-keto acids in biological matrices. Eventually, we demonstrated that the developed protocol is suited to measure mass isotopomers of these α-keto acids in tracer studies with stable isotopes. In conclusion, the here described method fills one of the last technical gaps for metabolomics investigations of central carbon metabolism.

  质谱法是研究细胞新陈代谢的一种功能强大、用途广泛的技术。其应用范围从代谢物的剖面分析到稳定同位素在生化反应网络中的精确定量和追踪。尽管该技术广泛应用于中心碳代谢，但大多数方法都无法对α-酮酸草酰乙酸、丙酮酸和乙醛酸进行准确评估，因为这些化合物在样品处理和质谱测量过程中会发生高度反应和降解。我们提出了一种衍生化程序，可在细胞代谢淬灭过程中以化学方式稳定这些化合物。通过超高压液相色谱耦合串联质谱法分析稳定的衍生物，可以准确地量化生物基质中α-酮酸的丰度。最后，我们证明了所开发的方案适用于在稳定同位素示踪研究中测量这些 α-酮酸的质量同位素。总之，本文所描述的方法填补了代谢组学研究中枢碳代谢的最后一个技术空白。
• α-(1-phenylhydrazino)-alkanone phenylhydrazones: The reaction with carbonyl compounds
  作者：Joachim G. Schantl、Peter Karpellus、Michael Prean

  DOI：10.1016/s0040-4020(01)87787-5

  日期：——

  The unsymmetrically disubstituted hydrazines 1 were condensed with carbonyl compounds. Some of the expected condensation products were isolated, but some were formed as unstable intermediates which underwent 1,4-elimination: The phenylhydrazone of the carbonyl compound used was obtained, together with the corresponding phenylazo-alkene 11 or alternatively, the 1,4-addition product of a different protic

  将不对称的二取代肼1与羰基化合物缩合。分离了一些预期的缩合产物，但一些形成了不稳定的中间体，这些中间体经过1,4-消除：获得了所用羰基化合物的苯hydr，以及相应的苯基偶氮-烯烃11或1,4-不同质子亲核试剂与11的加成产物。
• Organotin(IV) complexes with pyruvic acid phenylhydrazone (HPAPD): synthesis, spectral characterization, and <i>in vitro</i> antibacterial activity
  作者：M.A. Salam、M.A. Affan、Fasihuddin B. Ahmad、MD. Azharul Arafath

  DOI：10.1080/00958972.2012.687104

  日期：2012.6.10

  and its organotin(IV) complexes (2–6) were assayed for in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Enterobacter aerogenes, Escherichia coli, and Salmonella typhi. The screening results show that 2–6 have better antibacterial activity than 1 and that 6 exhibits significantly better activity than 2–5.

  丙酮酸苯腙 [HPAPD, (1)] 与氯化有机锡 (IV) 的反应导致形成五种新的有机锡 (IV) 配合物：[MeSnCl2(PAPD)] (2)、[BuSnCl2(PAPD) ] (3)、[PhSnCl2(PAPD)](4)、[Me2SnCl(PAPD)](5)和[Ph2SnCl(PAPD)](6)。配体 [HPAPD, (1)] 及其有机锡 (IV) 配合物 (2-6) 已通过 CHN 分析、摩尔电导率、UV-Vis、FT-IR、1H、13C 和 119Sn NMR 光谱研究进行表征。光谱数据表明，HPAPD 通过羧基-O 和偶氮甲碱-N 作为单负二齿螯合剂与锡（IV）配位；锡的配位数是五。测定了化合物 1 及其有机锡 (IV) 复合物 (2-6) 对金黄色葡萄球菌、枯草芽孢杆菌、产气肠杆菌、大肠杆菌和伤寒沙门氏菌的体外抗菌活性。

表征谱图