4-bromo-5-(4-chlorophenyl)-3-hydroxyfuran-2(5H)-one | 42393-16-8

• 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: 4-bromo-5-(4-chlorophenyl)-3-hydroxyfuran-2(5H)-one
• 英文别名: 3-bromo-2-(4-chlorophenyl)-4-hydroxy-2H-furan-5-one
• CAS: 42393-16-8
• 化学式: C₁₀H₆BrClO₃
• 分子量: 289.513
• InChiKey: USEFYQZCXYNZKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-5-(4-chlorophenyl)-3-hydroxyfuran-2(5H)-one 在 sodium hydroxide 、 双氧水 、 硫酸 作用下， 以 水 为溶剂， 反应 1.0h， 以61.3%的产率得到2-bromo-3-(4-chlorophenyl)-2-propenoic acid
  参考文献：
  名称：

  Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents

  摘要：

  In search for novel anti-cancer and anti-microbial agents with promising pharmacotoxicological profile, the synthesis of some substituted 4-halofuran-2(5H)-ones (8a-l, 9, 11) and derived halogenated quinoxalin-2(1H)-ones (12a-d) is described. Some of the halogenated furanones were readily oxidized to the corresponding 2-bromo-2-propenoic acids (13a-c) with hydrogen peroxide in alkaline medium. Twenty-two compounds were preliminary tested for their in vitro activity against three bacteria and one fungus and revealed encouraging activity. On the other hand, three compounds were screened as anti-cancer agents using cell line panel protocol and 22 compounds were subjected to cycline-dependent kinases (CDKs) inhibition screening program but were inactive.

  DOI：

  10.1007/s00044-010-9394-2
• 作为产物：
  描述：

  (E)-4-(4-氯苯基)-2-氧代丁-3-烯酸 在 水 、 溴 作用下， 以 氯仿 为溶剂， 反应 2.25h， 生成 4-bromo-5-(4-chlorophenyl)-3-hydroxyfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents

  摘要：

  In search for novel anti-cancer and anti-microbial agents with promising pharmacotoxicological profile, the synthesis of some substituted 4-halofuran-2(5H)-ones (8a-l, 9, 11) and derived halogenated quinoxalin-2(1H)-ones (12a-d) is described. Some of the halogenated furanones were readily oxidized to the corresponding 2-bromo-2-propenoic acids (13a-c) with hydrogen peroxide in alkaline medium. Twenty-two compounds were preliminary tested for their in vitro activity against three bacteria and one fungus and revealed encouraging activity. On the other hand, three compounds were screened as anti-cancer agents using cell line panel protocol and 22 compounds were subjected to cycline-dependent kinases (CDKs) inhibition screening program but were inactive.

  DOI：

  10.1007/s00044-010-9394-2

文献信息

• Ionic Liquid [BDBDMIm](Br3)2 As a New Efficient Brominating Agent in the Synthesis of γ-Butyrolactones
  作者：L. Z. Fekri

  DOI：10.1134/s1070363218050286

  日期：2018.5

  gamma-Butyrolactones can be synthesized by a solvent free multicomponent reaction of aldehydes with ethylpyruvate followed by an intramolecular cyclization using the new brominating agent, ionic liquid [BDBDMIm](Br-3)(2). This is the first synthesis of gamma-butyrolactones starting with aldehydes via the Knovenagel condensation and halogenation, followed by multicomponent cyclization reaction. The present method offers several advantages such as solvent free mild conditions, simple procedure, excellent yields, and environmental friendliness. All synthesized compounds were characterized by their IR, H-1 and C-13 NMR spectra.
• Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents
  作者：Alaa A. El-Tombary、Yasser S. Abdel-Ghany、Ahmad S. F. Belal、Shams A. Shams El-Dine、Farid S. G. Soliman

  DOI：10.1007/s00044-010-9394-2

  日期：2011.9

  In search for novel anti-cancer and anti-microbial agents with promising pharmacotoxicological profile, the synthesis of some substituted 4-halofuran-2(5H)-ones (8a-l, 9, 11) and derived halogenated quinoxalin-2(1H)-ones (12a-d) is described. Some of the halogenated furanones were readily oxidized to the corresponding 2-bromo-2-propenoic acids (13a-c) with hydrogen peroxide in alkaline medium. Twenty-two compounds were preliminary tested for their in vitro activity against three bacteria and one fungus and revealed encouraging activity. On the other hand, three compounds were screened as anti-cancer agents using cell line panel protocol and 22 compounds were subjected to cycline-dependent kinases (CDKs) inhibition screening program but were inactive.