(E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one | 1352347-04-6

• 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)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 1352347-04-6
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: CIADKJFJYZARIL-SOFGYWHQSA-N

物化性质

• 熔点：
  117-120 °C(Solv: ethanol (64-17-5))
• 沸点：
  472.4±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟乙醇 、 (E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 bis(η3-allyl-μ-chloropalladium(II)) 、 caesium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 0.83h， 以85%的产率得到(E)-3-(3,4-dimethoxyphenyl)-1-(3-(2-fluoroethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  A general and efficient Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones

  摘要：

  An efficient unprecedented Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones has been unveiled. The oxygen nucleophiles (fluoroalcohols) experience the rapid C-O bond forming reaction for the first time, albeit the alcohols are known to be a weak nucleophile and have greater competing beta-hydride elimination in the transition-metal-catalyzed (especially Pd and Cu) C-O cross-coupling reaction. The higher fluoroalcohols have also been effectively coupled with bromo-chalcones with relatively lower rate. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2016.04.013
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 3'-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以89.25%的产率得到(E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cdc25B inhibitory activity evaluation of chalcones

  摘要：

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。

  DOI：

  10.1007/s10600-013-0563-7

文献信息

• Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in TNFα-induced nuclear factor-κB activation inhibition
  作者：Yinglin Zuo、Yi Yu、Shuni Wang、Weiyan Shao、Binhua Zhou、Li Lin、Zhuoyu Luo、Ruogu Huang、Jun Du、Xianzhang Bu

  DOI：10.1016/j.ejmech.2012.02.023

  日期：2012.4

  A series of biaryl-based chalcones were designed as a combination of the natural chalcone and biphenyl moieties, and synthesized by two step chemistry involving Knoevenagel reaction and microwave assistant Suzuki coupling. Sulforhodamine B (SRB) assay was performed to evaluate the cell viability inhibitory abilities of these compounds against five cancer cell lines (A549, CNE2, SW480, MCF-7, and HepG2) from different tissues. Their Nuclear Factor-kappa B (NF-kappa B) nuclear translocation inhibitory activities were further investigated by High Content Analysis (HCA) based assay. Most of the compounds showed moderate to strong anticancer and NF-kappa B nuclear translocation inhibition activities and potent compounds were found. (C) 2012 Elsevier Masson SAS. All rights reserved.