(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.
• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  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。
• A general and efficient Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones
  作者：T.M. Rangarajan、Kavita Devi、Akhilesh K. Verma、Rishi Pal Singh、Raj Pal Singh

  DOI：10.1016/j.jfluchem.2016.04.013

  日期：2016.6

  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.