N-{2,2-bis[(4-chlorophenyl)sulfanyl]-1-cyanoethenyl}acetamide | 537709-53-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-{2,2-bis[(4-chlorophenyl)sulfanyl]-1-cyanoethenyl}acetamide
• 英文别名: N-[2,2-bis[(4-chlorophenyl)sulfanyl]-1-cyanoethenyl]acetamide
• CAS: 537709-53-8
• 化学式: C₁₇H₁₂Cl₂N₂OS₂
• mdl: MFCD03464197
• 分子量: 395.333
• InChiKey: JLKNBQRYGFKQBV-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  554.0±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-{2,2-bis[(4-chlorophenyl)sulfanyl]-1-cyanoethenyl}acetamide 在 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 以56%的产率得到5-[(4-Chlorophenyl)sulfanyl]-2-methyl-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：

  2-acetylamino-3,3-dichloroacrylonitrile 、 4-氯苯硫酚 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以80%的产率得到N-{2,2-bis[(4-chlorophenyl)sulfanyl]-1-cyanoethenyl}acetamide
  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

文献信息

• ——
  作者：S. G. Pil'o

  DOI：10.1023/a:1023333011230

  日期：——

  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.