Methyl 2-phenyl-5-sulfanyl-1,3-oxazole-4-carboxylate | 83990-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 2-phenyl-5-sulfanyl-1,3-oxazole-4-carboxylate
• CAS: 83990-18-5
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: VFPURCAOOLUERH-UHFFFAOYSA-N

物化性质

• 熔点：
  127-130 °C
• 沸点：
  394.0±52.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  53.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-phenyl-5-sulfanyl-1,3-oxazole-4-carboxylate 以 甲醇 为溶剂， 以70%的产率得到5-(4-methoxycarbonyl-2-phenyl-thiazol-5-ylsulfanyl)-2-phenyl-oxazole-4-carboxylic acid methyl ester
  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：

  methyl ester of 3,3-dichloro-2-benzoylaminoacrylic acid 在 sodium hydrogensulfide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以64%的产率得到Methyl 2-phenyl-5-sulfanyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Vinogradova, T. K.; Kisilenko, A. A.; Drach, B. S., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1630 - 1635

  摘要：

  DOI：

文献信息

• VINOGRADOVA, T. K.;KISILENKO, A. A.;DRACH, B. S., ZH. ORGAN. XIMII, 1982, 18, N 9, 1864-1869
  作者：VINOGRADOVA, T. K.、KISILENKO, A. A.、DRACH, B. S.

  DOI：——

  日期：——