2-(2-hydroxyphenyl)benzo[d]oxazole-6-carboxylic acid | 372516-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-hydroxyphenyl)benzo[d]oxazole-6-carboxylic acid
• CAS: 372516-32-0
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: ADXIZYAZACKXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyphenyl)benzo[d]oxazole-6-carboxylic acid 、 glucosamine hydrochloride 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以21%的产率得到2-(2-hydroxyphenyl)-N-((2R,3S,4S,5R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzo[d]oxazole-6-carboxamide
  参考文献：
  名称：

  Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

  摘要：

  A dual-emissive biopolymeric amphiphile (GC-HBO) has been prepared by densely conjugating hydrophilic glycol chitosan (GC) with a phototautomerizable hydrophobic dye (a derivative of 2-(2'-hydroxyphenyl) benzoxazole, HBO) showing excited-state intramolecular proton transfer (ESIPT). Ratiometric modulation of phototautomeric (enol-keto) dual emission, governed by the chromophoric aggregation state, was studied with a low-molecular-weight model compound (GA-HBO) and was well correlated with the nanoparticle-forming behavior of GC-HBO via amphiphilic self-assembly in water. It has been found that the promoted chromophoric aggregation at higher concentration or at basic-to-neutral pH assists the nanostructure formation to generate predominant keto emission while the enol emission is intensified at lower concentration or with decreasing pH by disintegration of self-assembled structure. The assembly-related advantageous potential of GC-HBO for probing self-concentration and surrounding pH has been demonstrated with the ratiometric determination of critical particulation concentration (0.04 kg m(-3)) and near-physiological pH sensitivity (pK(a) similar to 5.1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.12.014
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸 在 lead(IV) tetraacetate 、 溶剂黄146 作用下， 反应 26.0h， 生成 2-(2-hydroxyphenyl)benzo[d]oxazole-6-carboxylic acid
  参考文献：
  名称：

  Concentration and pH-modulated dual fluorescence in self-assembled nanoparticles of phototautomerizable biopolymeric amphiphile

  摘要：

  A dual-emissive biopolymeric amphiphile (GC-HBO) has been prepared by densely conjugating hydrophilic glycol chitosan (GC) with a phototautomerizable hydrophobic dye (a derivative of 2-(2'-hydroxyphenyl) benzoxazole, HBO) showing excited-state intramolecular proton transfer (ESIPT). Ratiometric modulation of phototautomeric (enol-keto) dual emission, governed by the chromophoric aggregation state, was studied with a low-molecular-weight model compound (GA-HBO) and was well correlated with the nanoparticle-forming behavior of GC-HBO via amphiphilic self-assembly in water. It has been found that the promoted chromophoric aggregation at higher concentration or at basic-to-neutral pH assists the nanostructure formation to generate predominant keto emission while the enol emission is intensified at lower concentration or with decreasing pH by disintegration of self-assembled structure. The assembly-related advantageous potential of GC-HBO for probing self-concentration and surrounding pH has been demonstrated with the ratiometric determination of critical particulation concentration (0.04 kg m(-3)) and near-physiological pH sensitivity (pK(a) similar to 5.1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.12.014