benzyl 5-phenyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylate | 1198279-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl 5-phenyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylate
• 英文别名: Benzyl 5-phenyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazole-4-carboxylate
• CAS: 1198279-52-5
• 化学式: C₂₆H₂₃NO₆
• 分子量: 445.472
• InChiKey: JZDGMLWPXFSNCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 5-phenyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylate 在 25% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以98%的产率得到5-phenyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylic acid
  参考文献：
  名称：

  Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

  摘要：

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.

  DOI：

  10.1021/jo9016265
• 作为产物：
  描述：

  benzyl 3-oxo-3-phenyl-2-(3,4,5-trimethoxybenzamido)propanoate 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到benzyl 5-phenyl-2-(3,4,5-trimethoxyphenyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

  摘要：

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.

  DOI：

  10.1021/jo9016265