2-pyrrolecarboxaldehyde phenylhydrazone | 81280-72-0

• 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-pyrrolecarboxaldehyde phenylhydrazone
• 英文别名: 2-((2-phenylhydrazono)methyl)-1H-pyrrole；1H-pyrrole-2-carbaldehyde phenylhydrazone；pyrrole-2-carboxaldehyde phenylhydrazone；Pyrrole-2-carboxaldehyde phenylhydrazone；N-(1H-pyrrol-2-ylmethylideneamino)aniline
• CAS: 81280-72-0
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: CKXVOVJLHCFQAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.9±24.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 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：
  40.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吡咯甲醛 、 苯肼,盐酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以98%的产率得到2-pyrrolecarboxaldehyde phenylhydrazone
  参考文献：
  名称：

  Open Vessel and Cooling while Heating Microwave-Assisted Synthesis of Pyridinyl N-Aryl Hydrazones

  摘要：

  We reported the first example of open vessel and cooling while heating microwave-assisted synthesis of pyridinyl N-aryl hydrazones. Compounds were prepared in excellent isolated yields (88-98%) in only 5 min, by reacting 4- and 2,4-(di) substituted phenylhydrazines, bearing both electron-donating (4-CH3, 4-OCH3) and -withdrawing (4-Cl, 4-Br, 4CF(3), 4-NO2, 2,4-Cl-2) groups with 2-, 3-, and 4-acetylpyridine. The method was successfully extended to other carbonyl compounds.

  DOI：

  10.1021/co100015b

文献信息

• Solubility of Thiophene-, Furan- and Pyrrole-2-Carboxaldehyde Phenylhydrazone Derivatives in 2.82 mol⋅L−1 Aqueous DMSO at 298.15 K, Inhibition of Lymphoproliferation and Tubulin Polymerization: A Study Based on the Scaled Particle Theory
  作者：Ysaías J. Alvarado、Melchor Álvarez-Mon、Joanna Baricelli、José Caldera-Luzardo、Néstor Cubillán、Gladys Ferrer-Amado、Manzur Hassanhi、Yovani Marrero-Ponce、Victoria Mancilla、Miguel A. Rocafull、María Esther San Antonio-Sánchez、José Ojeda-Andara、Luz E. Thomas

  DOI：10.1007/s10953-010-9568-z

  日期：2010.10

  In this work, the solubilities of nine phenylhydrazone derivatives in water and in 2.82 mol⋅L−1 aqueous DMSO at 298.15 K, expressed on the molar fraction scale, are reported. The estimated value of the standard Gibbs energy for transferring the solute from water to 2.82 mol⋅L−1 DMSO, $\Delta G^0}_\mathrmW}\rightarrow \mathrmmix}}$ , for each system, indicates that it is a spontaneous process. Some of the phenylhydrazone derivatives inhibited the induction of T lymphocyte proliferation by phytohaemagglutinin (PHA) but only DPCT and NPCF efficiently inhibited Guinea pig brain tubulin polymerization. Scaled Particle Theory (SPT) was used to interpretate solubility and biological activity results. Based on the results we suggested that the difference in the work of cavity creation ΔΔG c, associated with the transfer of the phenylhydrazone derivatives from water to 2.82 mol⋅L−1 aqueous DMSO, is the dominant factor in the magnitude of $\Delta G^0}_\mathrmW}\rightarrow \mathrmmix}}$ . The later quantity was considered to be an indirect measurement of the hydrophobic character of these derivatives, and it can be used to interpret the biological results.

  本研究报告了在 298.15 K 时，九种苯基腙衍生物在水中和 2.82 mol⋅L-1 二甲基亚砜水溶液中的溶解度（以摩尔分数表示）。每个体系将溶质从水中转移到 2.82 mol⋅L-1 DMSO 中的标准吉布斯能的估计值 $\Delta G^0}_\mathrmW}\rightarrow \mathrmmix}}$ 表明这是一个自发过程。一些苯腙衍生物抑制了植物血凝素（PHA）对 T 淋巴细胞增殖的诱导作用，但只有 DPCT 和 NPCF 能有效抑制豚鼠脑小管蛋白的聚合。我们采用缩放粒子理论（SPT）来解释溶解度和生物活性结果。根据研究结果，我们认为，苯腙衍生物从水中转移到 2.82&nbSP;mol⋅L-1 的二甲基亚砜水溶液时，空穴形成功 ΔΔG c 的差异是影响 $\Delta G^0}_\mathrmW}\rightarrow \mathrmmix}}$ 大小的主要因素。后一个量被认为是对这些衍生物疏水性的间接测量，可用来解释生物学结果。
• Electrochemical Synthesis of Pyrazolines and Pyrazoles via [3+2] Dipolar Cycloaddition
  作者：Martin Linden、Silja Hofmann、Antonia Herman、Nicole Ehler、Robin M. Bär、Siegfried R. Waldvogel

  DOI：10.1002/anie.202214820

  日期：2023.2.20

  Electrochemically initiated [3 2] cycloaddition reactions of readily available and less toxic starting materials enable a facile synthesis of pyrazolines and pyrazoles. Application of a biphasic system and sodium iodide in a dual role as mediator and electrolyte allows for selective reactions with outstanding robustness towards scalability.

  电化学引发的 [3 2] 环加成反应容易获得且毒性较低的起始材料使吡唑啉和吡唑的合成变得容易。双相系统和碘化钠作为介质和电解质的双重作用的应用允许选择性反应对可扩展性具有出色的鲁棒性。
• Synthesis, and docking studies of arylhydrazone compounds and evaluation of their platelet aggregation inhibitory effect and cytotoxicity
  作者：Maryam H. Klidsar、Marjan Esfahanizadeh、Pantea Haghverdi、Salimeh Amidi、Farzad Kobarfard

  DOI：10.1007/s00044-022-02931-w

  日期：2022.9