(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-[2-chloro-6-methoxy-4-(methylsulfanyl)pyrimidin-5-yl]-1-phenyl-prop-2-en-1-ol | 1449464-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-[2-chloro-6-methoxy-4-(methylsulfanyl)pyrimidin-5-yl]-1-phenyl-prop-2-en-1-ol
• 英文别名: (E)-1-(1,3-benzodioxol-5-yl)-1-(4-chloro-6-methoxy-2-methylsulfanylpyrimidin-5-yl)-3-phenylprop-2-en-1-ol
• CAS: 1449464-83-8
• 化学式: C₂₂H₁₉ClN₂O₄S
• 分子量: 442.923
• InChiKey: JHWNHNFUODYKPB-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-[2-chloro-6-methoxy-4-(methylsulfanyl)pyrimidin-5-yl]-1-phenyl-prop-2-en-1-ol 在 氢溴酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 0.5h， 生成 7-(benzo[d][1,3]dioxol-5-yl)-4-methoxy-2-methylsulfanyl-5-phenyl-7H-thiopyrano[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis of 7H-Thiopyrano[2,3-d]pyrimidines by Hydrobromic Acid-Mediated Cyclization of 1-[4-(1,1-Dimethylethylsulfanyl)pyrimidin-5-yl]prop-2-en-1-ols

  摘要：

  7-Aryl- or 5,7-diaryl-4-methoxy-2-methylsulfanyl-7H-thiopyrano[2,3-d]pyrimidines have been prepared in satisfactory overall yields starting from 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine by a facile three-step sequence. 4-Chloro-5-lithio-6-methoxy-2-(methylsulfanyl)pyrimidine was generated by the treatment of 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine with LDA and was allowed to react with 3-arylprop-2-enals (cinnamaldehyde and its derivatives) or 1,3-diarylprop-2-en-1-ones (chalcone and its derivatives) to give the corresponding 3-aryl- or 1,3-diaryl-1-(4-chloropyrimidin-5-yl)prop-2-en-1-ol derivatives, respectively. Substitution of the 4-chloro group with sodium 1,1-dimethylethylthiolate gave 3-aryl- or 1,3-diaryl-1-[4-(1,1-dimethylethylsulfanyl)pyrimidin-5-yl]prop-2-en-1-ol derivatives, of which treatment with an equivalent of hydrobromic acid provided the desired products.

  DOI：

  10.3987/com-13-12677
• 作为产物：
  描述：

  (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-phenylprop-2-en-1-one 、 6-甲氧基-2-甲硫基-4-氯嘧啶 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以68%的产率得到(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-[2-chloro-6-methoxy-4-(methylsulfanyl)pyrimidin-5-yl]-1-phenyl-prop-2-en-1-ol
  参考文献：
  名称：

  Synthesis of 7H-Thiopyrano[2,3-d]pyrimidines by Hydrobromic Acid-Mediated Cyclization of 1-[4-(1,1-Dimethylethylsulfanyl)pyrimidin-5-yl]prop-2-en-1-ols

  摘要：

  7-Aryl- or 5,7-diaryl-4-methoxy-2-methylsulfanyl-7H-thiopyrano[2,3-d]pyrimidines have been prepared in satisfactory overall yields starting from 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine by a facile three-step sequence. 4-Chloro-5-lithio-6-methoxy-2-(methylsulfanyl)pyrimidine was generated by the treatment of 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine with LDA and was allowed to react with 3-arylprop-2-enals (cinnamaldehyde and its derivatives) or 1,3-diarylprop-2-en-1-ones (chalcone and its derivatives) to give the corresponding 3-aryl- or 1,3-diaryl-1-(4-chloropyrimidin-5-yl)prop-2-en-1-ol derivatives, respectively. Substitution of the 4-chloro group with sodium 1,1-dimethylethylthiolate gave 3-aryl- or 1,3-diaryl-1-[4-(1,1-dimethylethylsulfanyl)pyrimidin-5-yl]prop-2-en-1-ol derivatives, of which treatment with an equivalent of hydrobromic acid provided the desired products.

  DOI：

  10.3987/com-13-12677