(E)-3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one | 955024-56-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(Biphenyl-3-yl)-1-(4-methoxyphenyl)prop-2-en-1-one；(E)-1-(4-methoxyphenyl)-3-(4-phenylphenyl)prop-2-en-1-one
• CAS: 955024-56-3
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: KMWZUECQAQRWGB-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 2-乙基-2-甲基-1,3-二氧杂烷 、 草酸 、 对甲苯磺酸 、 sodium fluoride 作用下， 以 1,4-二氧六环 、 二乙二醇二甲醚 、 苯 为溶剂， 反应 20.0h， 生成 2-Biphenyl-4-yl-3-fluoro-5-(4-methoxy-phenyl)-furan
  参考文献：
  名称：

  一种将二氟卡宾环加成到α，β-不饱和醛和酮的新方法：合成Gem-二氟环丙基酮和2-氟呋喃。

  摘要：

  从二氟卡宾的[1 + 2]环加成到α，β-不饱和芳族醛和酮的1,3-二氧戊环上，可以容易地以中等收率获得一系列的宝石-二氟环丙基缩醛和缩酮。这些氟化化合物在酸性条件下的水解可通过分子内碳原子重排并同时裂解环而得到相应的宝石二氟环丙基酮或1-芳基-2-氟呋喃衍生物。

  DOI：

  10.1039/b212232d
• 作为产物：
  描述：

  对苯基苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers

  摘要：

  背景：许多合成支架物以及天然产物被确定为有效的抗氧化剂。本研究涉及对不同取代、具有药用特性的化合物类别“查尔酮和双查尔酮”进行抗氧化潜力评估。 方法：对一系列合成查尔酮1-13和双查尔酮14-18进行体外自由基清除活性测试。 结果：所有分子1-18在IC50范围内显示出明显的2,2-二苯基-1-苯基-亚硝基肼（DPPH）和2,2'-联苯二(3-乙基苯并噻唑啉-6-磺酸)（ABTS）自由基清除潜力，分别为0.58 ± 0.14 - 1.72 ± 0.03和0.49 ± 0.3 - 1.48 ± 0.06 μM。抗坏血酸（DPPH和ABTS的IC50分别为0.5 ± 0.1和0.46 ± 0.17 μM）被用作标准自由基清除剂。 结论：结构活性关系（SAR）显示了各种基团，包括-SMe和-OMe在清除活性中的积极参与。

  DOI：

  10.2174/1570180817999201001155032

文献信息

• Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
  作者：Yi-Fan Chang、Yi-Rui Jiang、Wei-Chieh Cheng

  DOI：10.1016/j.tetlet.2007.11.064

  日期：2008.1

  The highly efficient and convenient protocol to prepare diverse α,β-unsaturated aldehydes, ketones, and acids via the parallel solid-phase synthesis is developed. The key sulfone linker cleavage strategy is performed by ozonolysis to generate a carbonyl moiety followed by base-mediated polymer-bound sulfinate elimination to release our desired molecules from the resin. All α,β-unsaturated carbonyl compounds

  开发了一种通过平行固相合成制备各种α，β-不饱和醛，酮和酸的高效便捷方案。关键的砜接头裂解策略是通过臭氧分解产生羰基部分，然后进行碱介导的与聚合物结合的亚磺酸酯消除反应，从而从树脂中释放出所需的分子。所有α，β-不饱和羰基化合物均以良好的纯度和收率制备，无需进一步纯化。
• Alkene Synthesis by Photo‐Wolff‐Kischner Reaction of Sulfur Ylides and <i>N</i> ‐Tosylhydrazones
  作者：Pan‐Pan Gao、Dong‐Mei Yan、Ming‐Hang Bi、Min Jiang、Wen‐Jing Xiao、Jia‐Rong Chen

  DOI：10.1002/chem.202102671

  日期：2021.10.13

  A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity

  首次开发了硫叶立德和 N-甲苯磺酰腙的可见光驱动和室温光沃尔夫-基施纳反应，以提供烯烃合成的模块化途径。60 多个实例证明了高官能团耐受性和广泛的底物范围。产品中的 E- 和 Z- 烯烃立体化学都可以以优异的立体选择性进行控制。一系列机理研究支持该反应应该通过自由基 - 负离子交叉途径进行，具体涉及将光生硫叶立德自由基阳离子添加到 N-甲苯磺酰腙形成碳负离子和随后的沃尔夫-基施纳过程。
• Water Compatible Multicomponent Cascade Suzuki/Heck-Aldol, Suzuki-Aldol-Suzuki, and Aldol-Suzuki-Aldol Reactions: An Ecofriendly Paradigm for Multiple CarbonCarbon Bond Formation in One Pot
  作者：Rajesh Kumar、Richa、Nitin H. Andhare、Amit Shard、Arun K. Sinha

  DOI：10.1002/chem.201303069

  日期：2013.10.25

  Aryls in hot water: A versatile strategy has been devised for the synthesis of biologically active biaryl(hetero)chalcones from readily available precursors (see scheme). The method is step, pot, and carbon economic, ligand‐free, devoid of toxic reagents/solvents, and has a wide substrate scope.

  热水中的芳基：已经设计了一种通用的策略，可以从容易获得的前体中合成具有生物活性的联芳基（杂）查耳酮（参见方案）。该方法是一步，罐和碳经济，无配体，无毒试剂/溶剂的方法，并且具有广泛的底物范围。
• Multicomponent Cascade Synthesis of Biaryl-Based Chalcones in Pure Water and in an Aqueous Micellar Environment
  作者：Nicola Armenise、Danilo Malferrari、Sara Ricciardulli、Paola Galletti、Emilio Tagliavini

  DOI：10.1002/ejoc.201600095

  日期：2016.7

  the resulting intermediates underwent an in-situ aldol condensation reaction to give biaryl(hetero)chalcones in good to excellent yields. When the protocol was applied to highly lipophilic or less reactive reagents, micellar catalysis was required for good results. To achieve this, we successfully used a new surfactant obtained from renewable resources that we recently designed. Furthermore, using

  具有挑战性的联芳基查尔酮的多组分级联合成在纯水和水性胶束系统中进行。该方案的第一步是在水性介质中进行简单的 Pd 催化、无配体和有氧 Suzuki-Miyaura 反应。事实证明，这对于芳基和杂芳基溴化物与不同芳基硼酸的偶联非常有效。随后，所得中间体进行原位羟醛缩合反应，以良好至极好的收率得到联芳基（杂）查耳酮。当该协议应用于高度亲脂性或反应性较低的试剂时，需要胶束催化才能获得良好的结果。为了实现这一目标，我们成功地使用了一种从我们最近设计的可再生资源中获得的新型表面活性剂。此外，使用这种添加剂，
• Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
  作者：Adebayo Tajudeen Bale、Khalid Mohammed Khan、Uzma Salar、Sridevi Chigurupati、Tolulope Fasina、Farman Ali、Kanwal、Abdul Wadood、Muhammad Taha、Sitansu Sekhar Nanda、Mehreen Ghufran、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.003

  日期：2018.9

  Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible alpha-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as alpha-amylase inhibitors. For that purpose, a library of substituted chalcones 1-13 and bis-chalcones 14-18 were synthesized and characterized by spectroscopic techniques EI-MS and H-1 NMR. CHN analysis was carried out and found in agreement with the calculated values. All compounds were evaluated for in vitro alpha-amylase inhibitory activity and demonstrated good activities in the range of IC50 = 1.25 +/- 1.05-2.40 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 1.04 +/- 0.3 mu M). Limited structure-activity relationship (SAR) was established by considering the effect of different groups attached to aryl rings on varying inhibitory activity. SMe group in chalcones and OMe group in bis-chalcones were found more influential on the activity than other groups. However, in order to predict the involvement of different groups in the binding interactions with the active site of alpha-amylase enzyme, in silico studies were also conducted.