5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carboxylic acid methyl ester | 537709-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 5-[(4-chlorophenyl)sulfanyl]-2-(4-methylphenyl)-1,3-oxazole-4-carboxylate；methyl 5-(4-chlorophenyl)sulfanyl-2-(4-methylphenyl)-1,3-oxazole-4-carboxylate
• CAS: 537709-75-4
• 化学式: C₁₈H₁₄ClNO₃S
• 分子量: 359.833
• InChiKey: GPNADBCRFGRSGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carboxylic acid methyl ester 在 氯化亚砜 、 水 、 溶剂黄146 、 N,N-二甲基苯胺 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 Methyl 2-benzamido-2-[5-[5-(4-chlorophenyl)sulfanyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]-1,3,4-oxadiazol-2-yl]acetate
  参考文献：
  名称：

  2-aryl-5-arylsulfanyl-1,3-oxazole-4-carboxylic acids and their derivatives

  摘要：

  A convenient preparative procedure has been developed for the synthesis of previously unknown 2-aryl- 5-arylsulfanyl-1,3-oxazole-4-carboxylic acids and their functional derivatives from accessible multicenter substrates of the general formula Cl(2)C=C(NHCOR)C(O)OMe. The products turned out to be suitable for various subsequent transformations. Some oxazole-4-carboxylic acid hydrazide derivatives containing a substituted oxazol-5-yl fragment at the N(2) atom in the hydrazine moiety underwent recyclization on heating in acetic acid; as a result, one oxazole ring was converted into 1,3,4-oxadiazole.

  DOI：

  10.1134/s1070363210070212
• 作为产物：
  描述：

  3,3-Dichloro-2-(4-methyl-benzoylamino)-acrylic acid methyl ester 在 三乙胺 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-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