4-(2-chloro-6-fluorophenyl)-2-[[4-(2-chloro-6-fluorophenyl)-5-cyano-6-oxo-1H-pyrimidin-2-yl]disulfanyl]-6-oxo-1H-pyrimidine-5-carbonitrile | 1228676-33-2

• 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: 4-(2-chloro-6-fluorophenyl)-2-[[4-(2-chloro-6-fluorophenyl)-5-cyano-6-oxo-1H-pyrimidin-2-yl]disulfanyl]-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 1228676-33-2
• 化学式: C₂₂H₈Cl₂F₂N₆O₂S₂
• 分子量: 561.379
• InChiKey: AKYRUZJDTFITID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-(2-chloro-6-fluorophenyl)-6-oxo-2-sulfanylidene-1,3-diazinane-5-carbonitrile 在 二甲基亚砜 作用下， 反应 0.17h， 以73%的产率得到6-(2-chloro-6-fluorophenyl)-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