6-(2,6-difluorophenyl)-4-oxo-2-sulfanylidene-1H-pyrimidine-5-carbonitrile | 1228676-37-6

• 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: 6-(2,6-difluorophenyl)-4-oxo-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
• CAS: 1228676-37-6
• 化学式: C₁₁H₅F₂N₃OS
• 分子量: 265.243
• InChiKey: RQLWUFMNLNWGOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(2,6-Difluorophenyl)-6-oxo-2-sulfanylidene-1,3-diazinane-5-carbonitrile 在 四氯苯醌 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以66%的产率得到6-(2,6-difluorophenyl)-4-oxo-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Some Observations on the Base-Catalyzed Cyclocondensation of 2,6-Dihalobenzaldehydes, Ethyl Cyanoacetate, and Thiourea

  摘要：

  The reaction of 2,6-difluorobenzaldehyde, 2-chloro-6-fluorobenzaldehyde, or 2,6-dichlorobenzaldehyde and ethyl cyanoacetate and thiourea, in the presence of potassium carbonate, yielded a mixture of the cis- and trans-5,6-dihydro-2-thiouracil derivatives 4a-c. Compounds 4a-c, which were found to be resistant to atmospheric oxidation even at high temperatures, were successfully dehydrogenated to 5a-c via prolonged heating with chloranil in toluene. Meanwhile, oxidation of the dihydro derivative 4b by heating in dimethylsufphoxide for 10min yielded the corresponding 2-thiouracil 5b in 73% yield, in addition to the disulfide derivative 7 as a minor product.

  DOI：

  10.1080/00397910903098730