methyl (2S)-2-[[2-[(5-methyl-2-phenyl-1,3-oxazole-4-carbonyl)amino]acetyl]amino]propanoate | 1257861-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[2-[(5-methyl-2-phenyl-1,3-oxazole-4-carbonyl)amino]acetyl]amino]propanoate
• CAS: 1257861-40-7
• 化学式: C₁₇H₁₉N₃O₅
• 分子量: 345.355
• InChiKey: KWTGEYNNQOGYNX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-甲基-2-苯基-1,3--恶唑-4-甲酸 、 H-Gly-L-Ala-OMe*TFA 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以31%的产率得到methyl (2S)-2-[[2-[(5-methyl-2-phenyl-1,3-oxazole-4-carbonyl)amino]acetyl]amino]propanoate
  参考文献：
  名称：

  A mild high yielding synthesis of oxazole-4-carboxylate derivatives

  摘要：

  Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-beta-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a beta-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.014

文献信息

• A mild high yielding synthesis of oxazole-4-carboxylate derivatives
  作者：Paula M.T. Ferreira、Elisabete M.S. Castanheira、Luís S. Monteiro、Goreti Pereira、Helena Vilaça

  DOI：10.1016/j.tet.2010.09.014

  日期：2010.11

  Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-beta-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a beta-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain. (C) 2010 Elsevier Ltd. All rights reserved.