4-(Diphenyl-phosphinoyl)-2-phenyl-5-p-tolylsulfanyl-oxazole | 537709-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(Diphenyl-phosphinoyl)-2-phenyl-5-p-tolylsulfanyl-oxazole
• 英文别名: 4-diphenylphosphoryl-5-(4-methylphenyl)sulfanyl-2-phenyl-1,3-oxazole
• CAS: 537709-78-7
• 化学式: C₂₈H₂₂NO₂PS
• 分子量: 467.528
• InChiKey: SARJPECJHXENSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(Diphenyl-phosphinoyl)-2-phenyl-5-p-tolylsulfanyl-oxazole 在 双氧水 、 溶剂黄146 作用下， 反应 8.0h， 以60%的产率得到4-(Diphenyl-phosphinoyl)-2-phenyl-5-(toluene-4-sulfonyl)-oxazole
  参考文献：
  名称：

  摘要：

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.

  DOI：

  10.1023/a:1023333011230
• 作为产物：
  描述：

  1-benzoylamino-2,2-bis(p-tolylthio)ethenyl(diphenyl)phosphine oxide 在 silver carbonate 作用下， 以 乙腈 为溶剂， 以60%的产率得到4-(Diphenyl-phosphinoyl)-2-phenyl-5-p-tolylsulfanyl-oxazole
  参考文献：
  名称：

  摘要：

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.

  DOI：

  10.1023/a:1023333011230