benzyl 2,5-diphenyloxazole-4-carboxylate | 1198279-44-5

• 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 2,5-diphenyloxazole-4-carboxylate
• 英文别名: Benzyl 2,5-diphenyl-1,3-oxazole-4-carboxylate
• CAS: 1198279-44-5
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: VYWRYBJQPWEMLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2,5-diphenyloxazole-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99%的产率得到2,5-diphenyloxazole-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：

  methyl 2-phenyl-2-oxazoline-4-carboxylate 在 silver(I) acetate 、 copper diacetate 、 palladium diacetate 、 potassium hydrogencarbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 benzyl 2,5-diphenyloxazole-4-carboxylate
  参考文献：
  名称：

  Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage

  摘要：

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。

  DOI：

  10.1039/c2cc00081d

文献信息

• Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage
  作者：Ziyuan Li、Ling Ma、Jinyi Xu、Lingyi Kong、Xiaoming Wu、Hequan Yao

  DOI：10.1039/c2cc00081d

  日期：——

  The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C–H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance.

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。
• Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
  作者：Juan F. Sanz-Cervera、Raül Blasco、Julio Piera、Michael Cynamon、Ignacio Ibáñez、Marcelo Murguía、Santos Fustero

  DOI：10.1021/jo9016265

  日期：2009.12.4

  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.