1-(furan-2-ylmethylene)-2-(4-nitrophenyl)hydrazine | 3155-21-3

• 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: 1-(furan-2-ylmethylene)-2-(4-nitrophenyl)hydrazine
• 英文别名: 2-furaldehyde 4-nitrophenylhydrazone；N-(furan-2-ylmethylideneamino)-4-nitroaniline
• CAS: 3155-21-3
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: ROUNDRXXZYHEHX-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  392.0±38.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  83.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-(furan-2-ylmethylene)-2-(4-nitrophenyl)hydrazine 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Synthesis and properties of pyrazolino[60]fullerene-donor systems

  摘要：

  A series of pyrazolino[60]fullerenes has been prepared in one pot by 1,3-dipolar cycloaddition to C-60 of the corresponding nitrile in-tine, which was generated in situ from the corresponding hydrazone. A range of donors and acceptors were introduced as substituents. Electrochemical and photophysical studies have revealed weak ground-state interactions between the organic addends and the fullerene sphere. Steady-state fluorescence has shown that, in both toluene and benzonitrile solutions, an efficient electron transfer process takes place when a strong donor is attached to the pyrazolino[60]fullerene system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00552-5
• 作为产物：
  描述：

  糠醛 、 4-硝基苯肼 生成 1-(furan-2-ylmethylene)-2-(4-nitrophenyl)hydrazine
  参考文献：
  名称：

  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

  摘要：

  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 $\Delta G^{0}_{\mathrm{W}\rightarrow \mathrm{mix}}$ 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 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 $\Delta G^{0}_{\mathrm{W}\rightarrow \mathrm{mix}}$ 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。

  DOI：

  10.1007/s10953-010-9568-z

文献信息

• 1,3-Dipolar cycloaddition of N-[4-nitrophenyl]-C-[2-furyl] nitrilimine with some dipolarophiles: A combined experimental and theoretical study
  作者：M. Bakavoli、F. Moeinpour、A. Davoodnia、A. Morsali

  DOI：10.1016/j.molstruc.2010.01.059

  日期：2010.4

  Abstract Reaction of vinyl acetate ( 3 ), 2-propyne-1-ol ( 4 ) and styrene ( 5 ) as dipolarphiles with N -[4-nitrophenyl]- C -[2-furyl] nitrilimine which was generated in situ has been shown to afford 3-(furan-2-yl)-1-(4-nitrophenyl)-4,5-dihydro-1 H -pyrazol-5-yl acetate ( 6 ), (3-(furan-2-yl)-1-(4-nitrophenyl)-1 H -pyrazol-5-yl)methanol ( 8 ) and 3-(furan-2-yl)-1-(4-nitrophenyl)-5-phenyl-4,5-dihydro-1

  摘要 乙酸乙烯酯 ( 3 )、2-丙炔-1-醇 ( 4 ) 和苯乙烯 ( 5 ) 作为偶极试剂与原位生成的 N -[4-硝基苯基]-C -[2-呋喃基]腈亚胺反应。显示提供 3-(呋喃-2-基)-1-(4-硝基苯基)-4,5-二氢-1H-吡唑-5-基乙酸酯 (6), (3-(呋喃-2-基) -1-(4-硝基苯基)-1H-吡唑-5-基)甲醇(8)和3-(呋喃-2-基)-1-(4-硝基苯基)-5-苯基-4,5-二氢-1 H-吡唑(10)。使用基于 DFT 的反应性指数研究这些反应的反应性和区域化学。
• Kaïm, Laurent El; Gautier, Laurent; Grimaud, Laurence, Synlett, 2003, # 12, p. 1844 - 1846
  作者：Kaïm, Laurent El、Gautier, Laurent、Grimaud, Laurence、Michaut, Valerie

  DOI：——

  日期：——
• 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 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。
• Synthesis and properties of pyrazolino[60]fullerene-donor systems
  作者：Eva Espı́ldora、Juan Luis Delgado、Pilar de la Cruz、Antonio de la Hoz、Vicente López-Arza、Fernando Langa

  DOI：10.1016/s0040-4020(02)00552-5

  日期：2002.7

  A series of pyrazolino[60]fullerenes has been prepared in one pot by 1,3-dipolar cycloaddition to C-60 of the corresponding nitrile in-tine, which was generated in situ from the corresponding hydrazone. A range of donors and acceptors were introduced as substituents. Electrochemical and photophysical studies have revealed weak ground-state interactions between the organic addends and the fullerene sphere. Steady-state fluorescence has shown that, in both toluene and benzonitrile solutions, an efficient electron transfer process takes place when a strong donor is attached to the pyrazolino[60]fullerene system. (C) 2002 Elsevier Science Ltd. All rights reserved.