N-cyclohexyl-5-(4-hydroxyphenyl)-2-methyl-1,3-oxazole-4-carboxamide | 1446876-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-cyclohexyl-5-(4-hydroxyphenyl)-2-methyl-1,3-oxazole-4-carboxamide
• CAS: 1446876-44-3
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: BDKGNVDGGWQKGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-乙酰氧基苯甲醛 在 溴 、 碳酸氢钠 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 N-cyclohexyl-5-(4-hydroxyphenyl)-2-methyl-1,3-oxazole-4-carboxamide
  参考文献：
  名称：

  Efficient Synthetic Approach to Fluorescent Oxazole-4-carboxylate Derivatives

  摘要：

  In our attempt to synthesize a halogenated analog of green fluorescent protein (GFP) chromophore, we discovered a simple and efficient synthetic strategy to the derivatives of oxazole-4-carboxylic acid substituted at positions 2 and 5. The method allows for introduction of different aryl substituents at the position 5, aryl or alkyl substituents at position 2 of oxazole, and gives access not only to free carboxyl at position 4, but also to a range of its amide derivatives. The advantages of the synthetic strategy presented are availability of precursors, good yields, and avoiding palladium coupling and metalation procedures. The synthesized compounds fluoresce in visible region with quantum yields up to 0.82. We believe that 5-aryl-4-carboxyoxazole is a promising core for creation of new fluorescent dyes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.706350

文献信息

• Efficient Synthetic Approach to Fluorescent Oxazole-4-carboxylate Derivatives
  作者：Mikhail S. Baranov、Konstantin A. Lukyanov、Pavel E. Ivashkin、Ilia V. Yampolsky

  DOI：10.1080/00397911.2012.706350

  日期：2013.9.2

  In our attempt to synthesize a halogenated analog of green fluorescent protein (GFP) chromophore, we discovered a simple and efficient synthetic strategy to the derivatives of oxazole-4-carboxylic acid substituted at positions 2 and 5. The method allows for introduction of different aryl substituents at the position 5, aryl or alkyl substituents at position 2 of oxazole, and gives access not only to free carboxyl at position 4, but also to a range of its amide derivatives. The advantages of the synthetic strategy presented are availability of precursors, good yields, and avoiding palladium coupling and metalation procedures. The synthesized compounds fluoresce in visible region with quantum yields up to 0.82. We believe that 5-aryl-4-carboxyoxazole is a promising core for creation of new fluorescent dyes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.