benzyl 2-(4-iodophenyl)oxazole-4-carboxylate | 1226954-70-6

• 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-(4-iodophenyl)oxazole-4-carboxylate
• CAS: 1226954-70-6
• 化学式: C₁₇H₁₂INO₃
• 分子量: 405.192
• InChiKey: ROASOEOPWIPBFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-(4-iodophenyl)oxazole-4-carboxylate 、 4-氯苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以58%的产率得到benzyl 2-(4'-chlorobiphenyl-4-yl)oxazole-4-carboxylate
  参考文献：
  名称：

  Utilization of the Suzuki Coupling to Enhance the Antituberculosis Activity of Aryloxazoles

  摘要：

  Potent antituberculosis aryl oxazoles can be made in an efficient three step process-formation of beta-hydroxy amides with serine benzyl ester; cyclization to afford oxazolines; and then dehydration to give the corresponding oxazoles. Furthermore, incorporation of an appropriate aryl halide allows utilization of the Suzuki cross coupling reaction to access new chemical space and more elaborate analogs. The compounds prepared by this method were shown to possess improved activity against M. tuberculosis, extremely low toxicity toward VERO cells and, as a result, high therapeutic indexes.

  DOI：

  10.3987/com-09-s(s)69
• 作为产物：
  描述：

  (S)-benzyl 2-(4-iodophenyl)-4,5-dihydrooxazole-4-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到benzyl 2-(4-iodophenyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Utilization of the Suzuki Coupling to Enhance the Antituberculosis Activity of Aryloxazoles

  摘要：

  Potent antituberculosis aryl oxazoles can be made in an efficient three step process-formation of beta-hydroxy amides with serine benzyl ester; cyclization to afford oxazolines; and then dehydration to give the corresponding oxazoles. Furthermore, incorporation of an appropriate aryl halide allows utilization of the Suzuki cross coupling reaction to access new chemical space and more elaborate analogs. The compounds prepared by this method were shown to possess improved activity against M. tuberculosis, extremely low toxicity toward VERO cells and, as a result, high therapeutic indexes.

  DOI：

  10.3987/com-09-s(s)69