2-phenyl-N-(pyrazin-2-yl)acetamide | 64750-84-1

• 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-phenyl-N-(pyrazin-2-yl)acetamide
• 英文别名: 2-phenyl-N-pyrazin-2-ylacetamide
• CAS: 64750-84-1
• 化学式: C₁₂H₁₁N₃O
• mdl: MFCD24389694
• 分子量: 213.239
• InChiKey: JPJFYUACGCBUEV-UHFFFAOYSA-N

物化性质

• 沸点：
  450.9±35.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氨基吡嗪 、 苯乙酸 在 硼酸三(2,2,2-三氟乙基)酯 作用下， 125.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以63%的产率得到2-phenyl-N-(pyrazin-2-yl)acetamide
  参考文献：
  名称：

  B(OCH₂CF₃)₃-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

  摘要：

  在环戊基甲醚（CPME）中，使用B(OCH2CF3)3直接对具有药用相关性的羧酸和胺进行酰胺化反应。

  DOI：

  10.1039/c5ob01801c

文献信息

• Synthesis, Crystal Structure, and Characterization of 2-Phenyl-<i>N</i>-(pyrazin-2-yl)Acetamide
  作者：Prakash S. Nayak、Badiadka Narayana、Sumati Anthal、Vivek K. Gupta、Rajni Kant

  DOI：10.1080/15421406.2013.840070

  日期：2014.3.24

  The title compound, 2-Phenyl-N-(pyrazin-2-yl)acetamide, C12H11N3O, was prepared by the coupling reaction and the product was crystallized by using toluene and methanol mixture(1:1) The structure of the compound was confirmed by elemental analysis, FTIR, H-1 NMR, thermogravimetric analysis, differential thermal analysis, UV-Visible spectroscopy, and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P 2(1)/c with the following unit-cell parameters: a = 8.1614(10), b = 14.9430(13), c = 9.3877(9) angstrom, beta = 103.653(12)degrees, and Z = 4. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0465 for 1486 observed reflections. An intramolecular CH center dot center dot center dot O hydrogen bond generates an S(6) graph-set motif. In the crystal, molecules are linked by NH center dot center dot center dot O and CH center dot center dot center dot O hydrogen bonds, forming a two-dimensional network.
• Synthesis, structural and vibrational investigation on 2-phenyl-N-(pyrazin-2-yl)acetamide combining XRD diffraction, FT-IR and NMR spectroscopies with DFT calculations
  作者：Jilu Lukose、C. Yohannan Panicker、Prakash S. Nayak、B. Narayana、B.K. Sarojini、C. Van Alsenoy、Abdulaziz A. Al-Saadi

  DOI：10.1016/j.saa.2014.07.004

  日期：2015.1

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 2-phenyl-N-(pyrazin-2-yl)acetamide have been investigated experimentally and theoretically using Gaussian09 software package. The title compound was optimized by using the HF/6-31G(6D,7F) and B3LYP/6-31G(6D,7F) calculations. The geometrical parameters are in agreement with the XRD data. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. Gauge-including atomic orbital H-1-NMR chemical shifts calculations were carried out and compared with experimental data. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. Molecular electrostatic potential was performed by the DFT method. First hyperpolarizability is calculated in order to find its role in non linear optics. From the XRD data, in the crystal, molecules are held together by strong C-H center dot center dot center dot O and N-H center dot center dot center dot O intermolecular interactions. (C) 2014 Elsevier B.V. All rights reserved.