2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfanyl]-1,3-oxazole-4-carbonitrile | 537709-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfanyl]-1,3-oxazole-4-carbonitrile
• 英文别名: 2-(4-methylphenyl)-5-(4-methylphenyl)sulfanyl-1,3-oxazole-4-carbonitrile
• CAS: 537709-68-5
• 化学式: C₁₈H₁₄N₂OS
• 分子量: 306.388
• InChiKey: HWEPURPEGBICRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfanyl]-1,3-oxazole-4-carbonitrile 在 双氧水 、 溶剂黄146 作用下， 反应 8.0h， 以54%的产率得到2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfonyl]-1,3-oxazole-4-carbonitrile
  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：

  N-(2,2-二氯-1-氰基乙烯基)-4-甲基苯甲酰胺 在 双氧水 、 溶剂黄146 、 三乙胺 、 silver carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 16.0h， 生成 2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfanyl]-1,3-oxazole-4-carbonitrile
  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