5-benzoyl-2-(4-chlorophenyl)-6-ethylthio-2,3-dihydrothiopyran-4-one | 874149-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzoyl-2-(4-chlorophenyl)-6-ethylthio-2,3-dihydrothiopyran-4-one
• 英文别名: 5-Benzoyl-2-(4-chlorophenyl)-6-ethylsulfanyl-2,3-dihydrothiopyran-4-one
• CAS: 874149-47-0
• 化学式: C₂₀H₁₇ClO₂S₂
• 分子量: 388.939
• InChiKey: RXFWDJROXPIJSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzoyl-2-(4-chlorophenyl)-6-ethylthio-2,3-dihydrothiopyran-4-one 、 甲胺 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以64%的产率得到5-benzoyl-2-(4-chlorophenyl)-6-methylamino-2,3-dihydrothiopyran-4-one
  参考文献：
  名称：

  [5C + 1S] Annulation:  A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones

  摘要：

  A facile and efficient synthetic route toward highly substituted 2,3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C + 1S] annulation of readily available alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na(2)S(.)9H(2)O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 51, an inhibitor of DNA-dependent protein kinase (DNA-PK).

  DOI：

  10.1021/jo052032g
• 作为产物：
  描述：

  (E)-2-[bis(ethylthio)methylene]-5-(4'-chlorophenyl)-1-phenylpent-4-ene-1,3-dione 在 sodium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以84%的产率得到5-benzoyl-2-(4-chlorophenyl)-6-ethylthio-2,3-dihydrothiopyran-4-one
  参考文献：
  名称：

  [5C + 1S] Annulation:  A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones

  摘要：

  A facile and efficient synthetic route toward highly substituted 2,3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C + 1S] annulation of readily available alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na(2)S(.)9H(2)O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 51, an inhibitor of DNA-dependent protein kinase (DNA-PK).

  DOI：

  10.1021/jo052032g

文献信息

• [5C + 1S] Annulation:  A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones
  作者：Xihe Bi、Dewen Dong、Yan Li、Qun Liu、Qian Zhang

  DOI：10.1021/jo052032g

  日期：2005.12.1

  A facile and efficient synthetic route toward highly substituted 2,3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C + 1S] annulation of readily available alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na(2)S(.)9H(2)O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 51, an inhibitor of DNA-dependent protein kinase (DNA-PK).