2-(imidazo[1,2-a]pyridin-2-yl)-2-oxoacetic acid | 1379572-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(imidazo[1,2-a]pyridin-2-yl)-2-oxoacetic acid
• 英文别名: 2-(imidazo[1,2-a]pyridin-2-yl)-2-oxoacetic acid radical；2-{Imidazo[1,2-a]pyridin-2-yl}-2-oxoacetic acid；2-imidazo[1,2-a]pyridin-2-yl-2-oxoacetic acid
• CAS: 1379572-69-6
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: LXXBSNVZCXLLJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(imidazo[1,2-a]pyridin-2-yl)-2-oxoacetic acid 在 硫酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以21%的产率得到
  参考文献：
  名称：

  Spontaneous resolution in a new chiral purely organic crystal containing homochiral helical chains: Synthesis, crystal structure, and phosphorescence

  摘要：

  A novel chiral purely organic crystal [(A)(HA(+)HSO(4)(-))(2)]center dot 2H(2)O (1) (A = 2-(imidazo [1,2-alpha]pyridin-2-yl)-2-oxoacetic acid) has been obtained through diffusion of acetone into sulfuric acid aqueous solution of A. This crystal was characterized by the elemental analysis, IR spectrum and the single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, chiral space group P2(1), with a = 10.092(2) angstrom, b = 15.641(3) angstrom, c = 10.551(2) angstrom, beta = 101.62(3)degrees, and Z = 2. Compound 1 reveals left-handed 2(1) helical chain assembled by hydrogen bond and hydrophobic (short atomic contact) interactions, in which spontaneous resolution occurs. The left-handed chirality of the original helical chain is transferred uniformly to adjacent chain in a homochiral manner, through interchain hydrogen bond and hydrophobic interactions, resulting in the formation of chiral layer. Compound 1 also exhibits green phosphorescence. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.12.057
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以80%的产率得到2-(imidazo[1,2-a]pyridin-2-yl)-2-oxoacetic acid
  参考文献：
  名称：

  Stacking-induced white-light and blue-light phosphorescence from purely organic radical materials

  摘要：

  基于新型纯有机自由基材料的内盐和钠盐分别表现出堆叠诱导的白光和蓝光磷光，并具有中等量子产率。它们在水中的高溶解度使其有望在有机发光二极管中得到潜在应用，尤其是作为白光发光二极管。

  DOI：

  10.1039/c1jm14690d

文献信息

• Anion–π interactions in new electron-deficient π systems: the relevance to solid phosphorescent colors
  作者：Guo-Ping Yong、Yi-Man Zhang、Wen-Long She

  DOI：10.1039/c2ce06702a

  日期：——

  molecule in crystal) to η1-type anion–π interactions (without guest methanol molecule in crystal). These carboxycarbonyl substituted imidazo[1,2-a]pyridinium salts also exhibit different phosphorescent colors in the solid state induced by crystal stacking structures or anion–π interactions that can influence the charge transfer to electron-deficient carboxycarbonyl substituted imidazo[1,2-a]pyridinium. Especially

  本文我们报告一个新的缺电子的π系统，即羧基羰取代咪唑并[1,2一]吡啶，其表现出不同的非共价相互作用（氢键，阴离子-π和η 1型阴离子π）与氯化或高氯酸根阴离子。晶体学结果表明，可以调节氯阴离子和π受体系统的相互作用类型：从阴离子与π的相互作用（与客体相互作用）甲醇在液晶分子）和η 1型阴离子-π相互作用（没有旅客甲醇晶体中的分子）。这些羧基羰基取代的咪唑并[1,2- a ]吡啶鎓盐在晶体堆积结构或阴离子-π相互作用下，也会表现出不同的固态磷光色，这会影响电荷向电子不足的羧基羰基取代的咪唑并[1,2-]的转移。一]吡啶。尤其是，由阴离子-π相互作用引起的固体磷光颜色变化非常有趣。高溶解度水 这些纯有机磷光材料有望成为潜在应用的候选材料。
• Excitation-light-responsive phosphorescent color changes in a β-cyclodextrin inclusion complex
  作者：Guo-Ping Yong、Bei Zhang、Yi-Man Zhang、Guang-Shui Li

  DOI：10.1039/c2jm31617j

  日期：——

  Herein, we report a novel supramolecular phosphorescent material based on a β-cyclodextrin inclusion complex. This inclusion complex exhibits unprecedented excitation-light-responsive phosphorescent color changes, which is a promising candidate for dynamically photofunctional material.

  在此，我们报告了一种基于δ-环糊精包合物的新型超分子磷光材料。这种包合复合物表现出前所未有的激发光响应磷光颜色变化，有望成为一种动态光功能材料。
• Spontaneous resolution in a new chiral purely organic crystal containing homochiral helical chains: Synthesis, crystal structure, and phosphorescence
  作者：Chen Shen、Yiman Zhang、Guoping Yong、Yumei Zhao

  DOI：10.1016/j.molstruc.2014.12.057

  日期：2015.3

  A novel chiral purely organic crystal [(A)(HA(+)HSO(4)(-))(2)]center dot 2H(2)O (1) (A = 2-(imidazo [1,2-alpha]pyridin-2-yl)-2-oxoacetic acid) has been obtained through diffusion of acetone into sulfuric acid aqueous solution of A. This crystal was characterized by the elemental analysis, IR spectrum and the single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic system, chiral space group P2(1), with a = 10.092(2) angstrom, b = 15.641(3) angstrom, c = 10.551(2) angstrom, beta = 101.62(3)degrees, and Z = 2. Compound 1 reveals left-handed 2(1) helical chain assembled by hydrogen bond and hydrophobic (short atomic contact) interactions, in which spontaneous resolution occurs. The left-handed chirality of the original helical chain is transferred uniformly to adjacent chain in a homochiral manner, through interchain hydrogen bond and hydrophobic interactions, resulting in the formation of chiral layer. Compound 1 also exhibits green phosphorescence. (C) 2014 Elsevier B.V. All rights reserved.
• Stacking-induced white-light and blue-light phosphorescence from purely organic radical materials
  作者：Guo-Ping Yong、Yi-Man Zhang、Wen-Long She、Ying-Zhou Li

  DOI：10.1039/c1jm14690d

  日期：——

  The internal salt and the sodium salt based on a new purely organic radical material exhibit stacking-induced white-light and blue-light phosphorescence, respectively, and possess moderate quantum yields. The high solubility in water makes them promising candidates for potential applications in OLEDs, especially as white-LEDs.

  基于新型纯有机自由基材料的内盐和钠盐分别表现出堆叠诱导的白光和蓝光磷光，并具有中等量子产率。它们在水中的高溶解度使其有望在有机发光二极管中得到潜在应用，尤其是作为白光发光二极管。