2-(1H-imidazole-1-yl)-3-methoxypyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1H-imidazole-1-yl)-3-methoxypyridine
• 英文别名: 2-(1H-imidazol-1-yl)-3-methoxypyridine；2-Imidazol-1-yl-3-methoxypyridine
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: PRXYHUVJSLCIPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-imidazole-1-yl)-3-methoxypyridine 在 三溴化硼 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 2-(3-butyl-1H-imidazolium-1-yl)pyridin-3-olate
  参考文献：
  名称：

  Solid-state fluorescence of zwitterionic imidazolium pyridinolates bearing long alkyl chains: Control of emission properties based on variation of lamellar alignment

  摘要：

  Herein, the control of the crystalline-state fluorescence of zwitterionic imidazolium 2-pyridin-3-olate 1 bearing linear alkyl chains via morphological variations is described, along with a mechanistic rationale. Crystals of 1a-e prepared from CH3CN exhibited intense blue fluorescence under UV irradiation at 298 K, whereas crystals of le prepared from i-PrOH/Et2O were less emissive under the same measurement conditions. Temperature-dependent emission spectra showed that emissive crystals of 1a-e experienced minimal emission decay with increasing temperature, whereas crystalline 1e, having a different polymorphism, was highly heat-quenchable. Single-crystal XRD established that less emissive, heat quenchable crystal le had a lamellar structure supported by consecutive face-to-face arrangement with 7c-stacking interactions between imidazolium and pyridinolate moieties, whereas highly emissive, heat-resistant crystals ld and le had a face-to-edge lamellar structure with CH-7r interactions between the heteroaromatic rings. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.08.045
• 作为产物：
  描述：

  咪唑 、 2-碘-3-甲氧基吡啶 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2-(1H-imidazole-1-yl)-3-methoxypyridine
  参考文献：
  名称：

  Solid-state fluorescence of zwitterionic imidazolium pyridinolates bearing long alkyl chains: Control of emission properties based on variation of lamellar alignment

  摘要：

  Herein, the control of the crystalline-state fluorescence of zwitterionic imidazolium 2-pyridin-3-olate 1 bearing linear alkyl chains via morphological variations is described, along with a mechanistic rationale. Crystals of 1a-e prepared from CH3CN exhibited intense blue fluorescence under UV irradiation at 298 K, whereas crystals of le prepared from i-PrOH/Et2O were less emissive under the same measurement conditions. Temperature-dependent emission spectra showed that emissive crystals of 1a-e experienced minimal emission decay with increasing temperature, whereas crystalline 1e, having a different polymorphism, was highly heat-quenchable. Single-crystal XRD established that less emissive, heat quenchable crystal le had a lamellar structure supported by consecutive face-to-face arrangement with 7c-stacking interactions between imidazolium and pyridinolate moieties, whereas highly emissive, heat-resistant crystals ld and le had a face-to-edge lamellar structure with CH-7r interactions between the heteroaromatic rings. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.08.045

文献信息

• Fluorescent Crystals of Zwitterionic Imidazolium Pyridinolates: A Rational Design for Solid-State Emission Based on the Twisting Control of Proemissive <i>N</i> -Aryl Imidazolium Platforms
  作者：Naruyoshi Komiya、Atsushi Yoshida、Di Zhang、Ryo Inoue、Soichiro Kawamorita、Takeshi Naota

  DOI：10.1002/ejoc.201700943

  日期：2017.9.15

  Zwitterionic imidazolium 2‐pyridin‐3‐olates exhibit intense blue emission at ambient temperature in the crystalline state, while other analogues such as 2‐phenolate and 3‐pyridin‐2‐olate are less emissive. XRD analyses and DFT calculations revealed that twisting control of arenolate functionalities is the key to obtaining efficient solid‐state fluorescence of the imidazolium–arenolate dyads.

  两性离子咪唑-2-吡啶-3-醇盐在室温下呈结晶态时会发出强烈的蓝光，而其他类似物（例如2-酚酸酯和3-吡啶-2-醇盐）的发射率较低。XRD分析和DFT计算表明，扭曲控制芳烃功能是获得咪唑鎓-芳烃二元体高效固态荧光的关键。
• One Step Conversion of Heteroaromatic-<i>N</i>-Oxides to Imidazolo-Heteroarenes
  作者：John M. Keith

  DOI：10.1021/jo702038g

  日期：2008.1.1

  [GRAPHICS]Various pyridine-, quinoline-, isoquinoline-, and pyrimidine-N-oxides were converted to their corresponding alpha-imida-zoloheteroarenes in good yield by treatment with. sulfuryl diimidazole in nonpolar solvents at elevated temperatures.
• Solid-state fluorescence of zwitterionic imidazolium pyridinolates bearing long alkyl chains: Control of emission properties based on variation of lamellar alignment
  作者：Atsushi Yoshida、Masahiro Ikeshita、Naruyoshi Komiya、Takeshi Naota

  DOI：10.1016/j.tet.2017.08.045

  日期：2017.10

  Herein, the control of the crystalline-state fluorescence of zwitterionic imidazolium 2-pyridin-3-olate 1 bearing linear alkyl chains via morphological variations is described, along with a mechanistic rationale. Crystals of 1a-e prepared from CH3CN exhibited intense blue fluorescence under UV irradiation at 298 K, whereas crystals of le prepared from i-PrOH/Et2O were less emissive under the same measurement conditions. Temperature-dependent emission spectra showed that emissive crystals of 1a-e experienced minimal emission decay with increasing temperature, whereas crystalline 1e, having a different polymorphism, was highly heat-quenchable. Single-crystal XRD established that less emissive, heat quenchable crystal le had a lamellar structure supported by consecutive face-to-face arrangement with 7c-stacking interactions between imidazolium and pyridinolate moieties, whereas highly emissive, heat-resistant crystals ld and le had a face-to-edge lamellar structure with CH-7r interactions between the heteroaromatic rings. (C) 2017 Elsevier Ltd. All rights reserved.