6-(6-chloro-2-fluorobenzyl)-2-{[(methylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one | 1242134-27-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(6-chloro-2-fluorobenzyl)-2-{[(methylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one
• 英文别名: 4-[(2-chloro-6-fluorophenyl)methyl]-2-(methylsulfanylmethylsulfanyl)-1H-pyrimidin-6-one
• CAS: 1242134-27-5
• 化学式: C₁₃H₁₂ClFN₂OS₂
• 分子量: 330.834
• InChiKey: PKQAVZIPOUUULV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(6-chloro-2-fluorobenzyl)-2-{[(methylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-thioxo-6-(2-fluoro-6-chlorobenzyl)-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  The specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides

  摘要：

  The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH(2)Cl, and MeSCH(2)Cl in the K(2)CO(3)-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.

  DOI：

  10.1007/s10593-010-0492-3
• 作为产物：
  描述：

  氯甲基甲硫醚 、 2-thioxo-6-(2-fluoro-6-chlorobenzyl)-2,3-dihydropyrimidin-4(1H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到6-(6-chloro-2-fluorobenzyl)-2-{[(methylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one
  参考文献：
  名称：

  The specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides

  摘要：

  The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH(2)Cl, and MeSCH(2)Cl in the K(2)CO(3)-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.

  DOI：

  10.1007/s10593-010-0492-3