7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one | 152719-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one
• 英文别名: 7-Methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one；7-methyl-2-phenylimidazo[1,2-a]pyrazin-3-one
• CAS: 152719-99-8
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: DGQHNBJMAAENRX-UHFFFAOYSA-N

物化性质

• 沸点：
  312.9±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-二苯基硫脲 、 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Rapid Quantification of the Activating Effects of Hydrogen-Bonding Catalysts with a Colorimetric Sensor

  摘要：

  A sensor has been developed to quickly and simply assess the relative reactivity of different hydrogen-bonding catalysts. Specifically, blue-shifts seen upon treatment of H-bonding catalysts with the colorimetric compound 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one correlate well to the K-eq of binding to the sensor. The blue-shifts also show a high degree of correlation with relative rates in Diels-Alder reactions of methyl vinyl ketone and cyclopentadiene employing the H-bonding catalysts. The relevance of the sensor blue-shifts to the LUMO-lowering abilities of the H-bonding catalysts is discussed.

  DOI：

  10.1021/ja3050663
• 作为产物：
  描述：

  2-phenylimidazo<1,2-a>pyrazin-3(7H)-one 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以69%的产率得到7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one
  参考文献：
  名称：

  咪唑并[1,2-a]吡嗪-3(7H)-one衍生物结构和光谱性质的基础研究

  摘要：

  2-甲基和2-苯基咪唑并[1,2-a]吡嗪-3(7H)-one 1和2及其N-和O-烷基化衍生物3-6的基本物理性质已通过X射线研究晶体学、紫外/可见吸收光谱、核磁共振和 AM1-COSMO 计算。3和4的晶体结构表明咪唑并[1,2-a]吡嗪-3(7H)-酮(咪唑并吡嗪酮)π-系统具有平面环结构和C3-O10键的弱羰基特征，表明咪唑并吡嗪酮π-系统具有两性离子共振结构的特性以增加芳香性。有关键长交替和 NMR 化学位移 1-4 的数据也支持它们的咪唑并吡嗪酮环具有小部分芳香特性。此外，咪唑并吡嗪酮衍生物 1-4 显示出由与氢键供体溶剂分子的氢键相互作用引起的溶剂化变色；衍生物 1 和 2 在它们的互变异构平衡中优选为 NH 形式的异构体。这些观察...

  DOI：

  10.1246/bcsj.76.2361

文献信息

• <i>N</i>-Vinyl and <i>N</i>-Aryl Hydroxypyridinium Ions: Charge-Activated Catalysts with Electron-Withdrawing Groups
  作者：George F. Riegel、Steven R. Kass

  DOI：10.1021/acs.joc.0c00498

  日期：2020.5.1

  the Diels-Alder reaction of cyclopentadiene with methyl vinyl ketone. These results along with kinetic isotope effect determinations revealed that the rate-determining step in the Friedel-Crafts transformations can shift from carbon-carbon bond formation to proton transfer to the catalyst's conjugate base. This leads to an inverted parabolic reaction rate profile and slower reactions with more acidic

  合成了具有吸电子取代基的电荷增强的布朗斯台德酸有机催化剂，并通过计算表征了其相对酸度，采用紫外可见活性传感器的1：1结合平衡常数（K1：1），与三乙基氧化膦配位时31P NMR发生了位移，一种情况是通过红外光谱法。测定了N-甲基吲哚与反式-β-硝基苯乙烯和2,2,2-三氟苯乙酮的Friedel-Crafts烷基化反应以及环戊二烯与甲基乙烯基酮的Diels-Alder反应的拟一级反应常数。这些结果以及动力学同位素效应测定表明，Friedel-Crafts转换中的速率确定步骤可以从碳-碳键形成转变为质子转移到催化剂的共轭碱。在某些情况下，这会导致抛物线反应速率曲线倒置以及与更多酸性催化剂的反应变慢。羟基吡啶鎓离子盐的N-乙烯基和N-芳基取代基上的吸电子基团提高了酸度，比三氟乙酸酸性更高的催化剂，并且Diels-Alder速率常数的对数与实测K1：1之间呈线性关系价值观。
• Quantification of Electrophilic Activation by Hydrogen-Bonding Organocatalysts
  作者：Ryan R. Walvoord、Phuong N. H. Huynh、Marisa C. Kozlowski

  DOI：10.1021/ja5086244

  日期：2014.11.12

  A spectrophotometric sensor is described that provides a useful assessment of the LUMO-lowering provided by catalysts in DielsAlder and FriedelCrafts reactions. A broad range of 33 hydrogen-bonding catalysts was assessed with the sensor, and the relative rates in the above reactions spanned 5 orders of magnitude as determined via H-1- and H-2 NMR spectroscopic measurements, respectively. The differences between the maximum wavelength shift of the sensor with and without catalyst (Delta lambda max(1)) were found to correlate linearly with ln(k(rel)) values for both reactions, even though the substrate feature that interacts with the catalyst differs significantly (ketone vs nitro). The sensor provides an assessment of both the inherent reactivity of a catalyst architecture as well as the sensitivity of the reaction to changes within an architecture. In contrast, catalyst pK(a) values are a poor measure of reactivity, although correlations have been identified within catalyst classes.
• Rapid Quantification of the Activating Effects of Hydrogen-Bonding Catalysts with a Colorimetric Sensor
  作者：Phuong N. H. Huynh、Ryan R. Walvoord、Marisa C. Kozlowski

  DOI：10.1021/ja3050663

  日期：2012.9.26

  A sensor has been developed to quickly and simply assess the relative reactivity of different hydrogen-bonding catalysts. Specifically, blue-shifts seen upon treatment of H-bonding catalysts with the colorimetric compound 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one correlate well to the K-eq of binding to the sensor. The blue-shifts also show a high degree of correlation with relative rates in Diels-Alder reactions of methyl vinyl ketone and cyclopentadiene employing the H-bonding catalysts. The relevance of the sensor blue-shifts to the LUMO-lowering abilities of the H-bonding catalysts is discussed.
• Fundamental Studies on the Structures and Spectroscopic Properties of Imidazo[1,2-<i>a</i>]pyrazin-3(7<i>H</i>)-one Derivatives
  作者：Shunichiro Nakai、Masanori Yasui、Masaki Nakazato、Fujiko Iwasaki、Shojiro Maki、Haruki Niwa、Mamoru Ohashi、Takashi Hirano

  DOI：10.1246/bcsj.76.2361

  日期：2003.12

  O-alkylated derivatives 3–6 have been investigated by X-ray crystallography, UV/vis absorption spectroscopy, NMR, and AM1-COSMO calculations. The crystal structures of 3 and 4 showed that the imidazo[1,2-a]pyrazin-3(7H)-one (imidazopyrazinone) π-system has a planar ring structure and a weakened carbonyl character of the C3–O10 bond, suggesting that the imidazopyrazinone π-system has the character of a zwitter-ionic

  2-甲基和2-苯基咪唑并[1,2-a]吡嗪-3(7H)-one 1和2及其N-和O-烷基化衍生物3-6的基本物理性质已通过X射线研究晶体学、紫外/可见吸收光谱、核磁共振和 AM1-COSMO 计算。3和4的晶体结构表明咪唑并[1,2-a]吡嗪-3(7H)-酮(咪唑并吡嗪酮)π-系统具有平面环结构和C3-O10键的弱羰基特征，表明咪唑并吡嗪酮π-系统具有两性离子共振结构的特性以增加芳香性。有关键长交替和 NMR 化学位移 1-4 的数据也支持它们的咪唑并吡嗪酮环具有小部分芳香特性。此外，咪唑并吡嗪酮衍生物 1-4 显示出由与氢键供体溶剂分子的氢键相互作用引起的溶剂化变色；衍生物 1 和 2 在它们的互变异构平衡中优选为 NH 形式的异构体。这些观察...