(E)-2,4-dichloro-1-(4-chlorostyryl)benzene | 59425-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2,4-dichloro-1-(4-chlorostyryl)benzene
• 英文别名: 2,4-dichloro-1-[(E)-2-(4-chlorophenyl)ethenyl]benzene
• CAS: 59425-82-0
• 化学式: C₁₄H₉Cl₃
• 分子量: 283.584
• InChiKey: GTOMVCOLARYJKL-DAFODLJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,4-二氯氯苄 在 sodium hydride 作用下， 以 乙腈 、 苯 为溶剂， 反应 12.0h， 生成 (E)-2,4-dichloro-1-(4-chlorostyryl)benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of some stilbene-based analogues

  摘要：

  The phytoalexin 3,5,4'-trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis(4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum.

  DOI：

  10.1007/s00044-010-9450-y

文献信息

• H₂SO₄-Promoted Synthesis of (<i>E</i>)-Stilbenes from Substituted Phenylacetones and Substituted Benzaldehydes Through Tandem Aldol–Grob Reaction
  作者：T. Narender、K. Papi Reddy、Sriniwas Tiwari

  DOI：10.1080/00397911.2010.488309

  日期：2011.5.3

  [image omitted] Stilbene derivates (stilbenoids) are present in plants and show a wide range of biological activities and potential therapeutic value. In continuation of our natural product synthesis program, an efficient, simple, and practical method has been developed to regioselectively synthesize (E)-stilbenes using H2SO4 as a catalyst in a short time (30-60s) at room temperature in good to excellent yields.
• COVIELLO V.; SIEGRIST A. E., HELV. CHIM. ACTA <HCAC-AV>, 1976, 59, NO 3, 802-819
  作者：COVIELLO V.、 SIEGRIST A. E.

  DOI：——

  日期：——
• Synthesis and biological evaluation of some stilbene-based analogues
  作者：Subhas S. Karki、Santosh R. Bhutle、Ganesh S. Pedgaonkar、P. K. Zubaidha、Rizwan M. Shaikh、Chitra G. Rajput、Girish S. Shendarkar

  DOI：10.1007/s00044-010-9450-y

  日期：2011.11

  The phytoalexin 3,5,4'-trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis(4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum.