(E)-3-(4-Chloro-phenyl)-1-(2,4-dichloro-5-fluoro-phenyl)-propenone | 259228-32-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-Chloro-phenyl)-1-(2,4-dichloro-5-fluoro-phenyl)-propenone
• 英文别名: 3-(4-Chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one；3-(4-chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one
• CAS: 259228-32-5
• 化学式: C₁₅H₈Cl₃FO
• 分子量: 329.585
• InChiKey: ASDGOPMPLKAWRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Chloro-phenyl)-1-(2,4-dichloro-5-fluoro-phenyl)-propenone 在 溴 作用下， 以 氯仿 为溶剂， 生成 2,3-dibromo-3-(4-chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)propan-1-one
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9
• 作为产物：
  描述：

  2,3-dibromo-3-(4-chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)propan-1-one 在 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (E)-3-(4-Chloro-phenyl)-1-(2,4-dichloro-5-fluoro-phenyl)-propenone
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9

文献信息

• A CONVENIENT SYNTHESIS OF 2,4-DIARYLPOLYHYDROQUINOLINE DERIVATIONS IN THE PRESENCE OF AMMONIUM ACETATE
  作者：Xiang-Shan Wang、Da-Qing Shi、Shu-Jiang Tu

  DOI：10.1081/scc-120014775

  日期：2002.1

  5-oxo-1,2,3,4,5,6,7,8-octahydroquinoline derivatives have been synthesized from 5,5-dimethyl-1,3-cyclohexane-dione (dimedone) and 1,3-diaryl-2-propen-1-one in DMF at 80°C in the presence of ammonium acetate with high yields (64–98%), the structure of the product was confirmed by X-ray analysis.

  摘要 从 5,5-二甲基-1,3-环己二酮（二甲酮）和 1, 合成了一系列取代的 5-氧代-1,2,3,4,5,6,7,8-八氢喹啉衍生物。 3-diaryl-2-propen-1-one 在 DMF 中于 80°C 在乙酸铵存在下以高产率 (64–98%)，通过 X 射线分析证实了产物的结构。
• Patel; Desai, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 199 - 201
  作者：Patel、Desai

  DOI：——

  日期：——
• Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines
  作者：Mari S. Karthikeyan、Bantwal S. Holla、Shalini Shenoy

  DOI：10.1007/s00706-007-0797-9

  日期：2008.6

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.