benzyl 2-methyl-5-phenyloxazole-4-carboxylate | 1198279-56-9

• 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-methyl-5-phenyloxazole-4-carboxylate
• 英文别名: Benzyl 2-methyl-5-phenyl-1,3-oxazole-4-carboxylate
• CAS: 1198279-56-9
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: WVUIJBMPDBBQOX-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  463.2±33.0 °C(predicted)
• 密度：
  1.194±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-methyl-5-phenyloxazole-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-methyl-5-phenyl-4-oxazolecarboxylic 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：

  (Z)-benzyl 2-acetamido-3-phenylacrylate 在 碘苯二乙酸 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以78%的产率得到benzyl 2-methyl-5-phenyloxazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization

  摘要：

  A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.

  DOI：

  10.1021/jo302073e

文献信息

• Cu(II)-catalyzed synthesis of 2,4,5-trisubstituted oxazoles
  作者：S. Prashanth、D.R. Adarsh、Rajashaker Bantu、Balasubramanian Sridhar、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2022.154252

  日期：2022.12

  for the synthesis of 2,4,5-trisubstituted oxazoles has been developed from the direct coupling of α-diazoketones with aryl or alkyl nitriles. The reaction proceeds through the formation of nitrilium ion by the nucleophic addition of nitrile onto diazo functionality followed by an intramolecular trapping of nitrilium ion by keto group. Both aryl, and alkyl nitriles underwent smooth cyclocondensation

  通过将 α-重氮酮与芳基或烷基腈直接偶联，开发了一种铜催化的简单有效的 2,4,5-三取代恶唑合成方案。通过将腈亲核加成到重氮官能团上，然后通过酮基在分子内捕获腈离子，反应通过形成腈离子进行。芳基腈和烷基腈均与重氮化合物顺利环化缩合，以优异的收率得到三取代的恶唑。
• CN115043787
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization
  作者：Yunhui Zheng、Xuming Li、Chengfeng Ren、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/jo302073e

  日期：2012.11.16

  A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.
• 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.