ethyl 2-(4-chlorophenyl)-6-methyl-4-sulfanylidene-1H-pyrimidine-5-carboxylate | 129226-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 2-(4-chlorophenyl)-6-methyl-4-sulfanylidene-1H-pyrimidine-5-carboxylate
• CAS: 129226-49-9
• 化学式: C₁₄H₁₃ClN₂O₂S
• 分子量: 308.788
• InChiKey: VPMVKGTWWVFQGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.98
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 、 ethyl 2-(4-chlorophenyl)-6-methyl-4-sulfanylidene-1H-pyrimidine-5-carboxylate 在 silica gel 作用下， 反应 0.01h， 以70%的产率得到ethyl 2-(4-chlorophenyl)-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)-6-methylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides

  摘要：

  Reaction of ethyl 4-thioxo-3,4-dihydropyrimidine-5-carboxylate derivatives 1a,b and ethyl 4-oxo-3,4-dihydropyrimidine-5-carboxylate 1c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in KOH or TEA afforded ethyl 2- aryl-4-(2',3',4',6'-tetra-O-acetyl-alpha-D-glucopyranosylthio or/oxy)-6-methylpyrimidine-5-carboxylate 6a-c. The glucosides 6a and 6b were obtained by the reaction of 1a and 1b with peracetylated glucose3 under MW irradiation. Mercuration of 1a followed by reaction with acetobromoglucose gave the same product 6a. The reaction of 1a-c with peracetylated ribose 4 under MW irradiation gave ethyl 2-aryl-4-(2',3',5'-tri-O-acetyl-alpha-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 8a-c. The deprotection of 6a-c and 8a-c in the presence of methanol and TEA/H2O afforded the deprotected products 7a-c and 9a-c. The structure were confirmed by using H-1 and (CNMR)-C-13 spectra. Selected members of these compounds were screened for antimicrobial activity.

  DOI：

  10.1080/15257770802271805

文献信息

• Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides
  作者：H. A. El-Sayed、A. H. Moustafa、A. Z. Haikal、I. M. Abdou、E. S. H. El-Ashry

  DOI：10.1080/15257770802271805

  日期：2008.8.28

  Reaction of ethyl 4-thioxo-3,4-dihydropyrimidine-5-carboxylate derivatives 1a,b and ethyl 4-oxo-3,4-dihydropyrimidine-5-carboxylate 1c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in KOH or TEA afforded ethyl 2- aryl-4-(2',3',4',6'-tetra-O-acetyl-alpha-D-glucopyranosylthio or/oxy)-6-methylpyrimidine-5-carboxylate 6a-c. The glucosides 6a and 6b were obtained by the reaction of 1a and 1b with peracetylated glucose3 under MW irradiation. Mercuration of 1a followed by reaction with acetobromoglucose gave the same product 6a. The reaction of 1a-c with peracetylated ribose 4 under MW irradiation gave ethyl 2-aryl-4-(2',3',5'-tri-O-acetyl-alpha-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 8a-c. The deprotection of 6a-c and 8a-c in the presence of methanol and TEA/H2O afforded the deprotected products 7a-c and 9a-c. The structure were confirmed by using H-1 and (CNMR)-C-13 spectra. Selected members of these compounds were screened for antimicrobial activity.