1-(3’,5’-dimethylbiphenyl-4-yl)ethanone | 677022-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3’,5’-dimethylbiphenyl-4-yl)ethanone
• 英文别名: 4-acetyl-3',5'-dimethyl-1,1'-biphenyl；1-(3',5'-Dimethyl-[1,1'-biphenyl]-4-yl)ethanone；1-[4-(3,5-dimethylphenyl)phenyl]ethanone
• CAS: 677022-27-4
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: UBMOPBKMERPGRG-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±11.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3’,5’-dimethylbiphenyl-4-yl)ethanone 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus

  摘要：

  Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.018
• 作为产物：
  描述：

  4-溴苯乙酮 、 3,5-二甲基苯硼酸 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到1-(3’,5’-dimethylbiphenyl-4-yl)ethanone
  参考文献：
  名称：

  可升华的双（β-亚氨基甲酸）钯（II）配合物及其在铃木-宫浦反应中的催化剂应用

  摘要：

  被两个β-亚氨基烯酸酯配体强烈螯合的Pd（II）络合物仅需两步即可轻松合成，并基于其可升华和高度稳定的特性进行纯化。锚固在二氧化硅表面的Pd（II）配合物在Suzuki-Miyaura反应中显示出良好的催化活性（使用0.05 mol％的催化剂，收率可达99％）。它们耐受温度范围广（rt〜110°C）和各种溶剂，并且经过简单的回收过程即可重复使用多次。

  DOI：

  10.1016/j.tetlet.2018.06.051

文献信息

• Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF
  作者：Qing Huang、Jiabin Qiu、Limei Li、Guohai Xu、Zhonggao Zhou

  DOI：10.1007/s11243-014-9847-4

  日期：2014.9

  Three new palladium catalysts, prepared via reactions of PdCl2 with readily obtained and inexpensive dicationic imidazolium salts, have been developed for the Suzuki reaction. The pre-catalyst was formed in situ using the imidazolium ligand, base and Pd metal precursor in 1,4-dioxane. This palladium catalyst provides a convenient and general method for the synthesis of biaryls from aryl bromides, activated

  通过 PdCl2 与容易获得且廉价的双阳离子咪唑鎓盐反应制备的三种新型钯催化剂已被开发用于 Suzuki 反应。使用咪唑鎓配体、碱和 Pd 金属前体在 1,4-二恶烷中原位形成预催化剂。这种钯催化剂提供了一种方便和通用的方法，用于在有氧条件下在含水 DMF 中从芳基溴化物、活化的芳基氯化物和含有吸电子取代基和给电子基团的芳基硼酸（19 个实例）合成联芳基化合物（所有 26 个实例）。图形摘要 三种由 PdCl2 制成的新型钯催化剂和容易获得的廉价双阳离子咪唑鎓盐已被开发用于 Suzuki 反应。
• Sublimable bis( β -iminoenolate)palladium(II) complexes and their application as catalysts in Suzuki-Miyaura reactions
  作者：Mi Jin Kim、Myung Jin Jung、Yeong Joon Kim、Ha Kyoung Sung、Ju Young Lee、Sung Jin Ham、Chan Pil Park

  DOI：10.1016/j.tetlet.2018.06.051

  日期：2018.8

  The Pd(II) complexes strongly chelated by two β-iminoenolate ligands were easily synthesized in only two steps, and purified based on their sublimable and highly stable property. The Pd(II) complexes anchored on a silica surface showed good catalytic activity in Suzuki-Miyaura reactions (up to 99% yield with 0.05 mol% catalyst). They tolerated a wide range of temperature (rt∼110 °C) and various solvents

  被两个β-亚氨基烯酸酯配体强烈螯合的Pd（II）络合物仅需两步即可轻松合成，并基于其可升华和高度稳定的特性进行纯化。锚固在二氧化硅表面的Pd（II）配合物在Suzuki-Miyaura反应中显示出良好的催化活性（使用0.05 mol％的催化剂，收率可达99％）。它们耐受温度范围广（rt〜110°C）和各种溶剂，并且经过简单的回收过程即可重复使用多次。
• Nanosized Bispyrazole-Based Cryptand-Stabilized Palladium(0) Nanoparticles: A Reusable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction in Water
  作者：Ashish Verma、Kapil Tomar、Parimal K. Bharadwaj

  DOI：10.1021/acs.inorgchem.8b03015

  日期：2019.1.22

  controlled synthesis and stabilization of ultrafine palladium nanoparticles (Pd NPs) of nearly ∼2 nm size. The as-synthesized Pd NPs were characterized by X-ray photoelectron spectroscopy, transmission electron microscopy, and powder X-ray diffraction. The well-dispersed cryptand-stabilized nanoparticles are found to catalyze the C–C bond-forming Suzuki–Miyaura reaction heterogeneously using water as a green

  合成了具有长刚性腔的大双环穴状配体，其在三个桥的每一个中均包含螯合的双吡唑部分。多个螯合金属结合位点可用于受控合成和稳定近2 nm尺寸的超细钯纳米颗粒（Pd NPs）。通过X射线光电子能谱，透射电子显微镜和粉末X射线衍射对合成后的Pd NP进行表征。发现分散良好的隐链稳定的纳米粒子可使用水作为绿色溶剂，以非均相的方式催化形成C–C键的Suzuki–Miyaura反应。
• A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki–Miyaura reaction in pure water under air
  作者：Qi Cai、Gaosheng Liang、Yufang Xu、Xuhong Qian、Weiping Zhu

  DOI：10.1039/c6ra11736h

  日期：——

  over mesoporous silica. Pd@FSM with a high palladium loading of ca. 11 mg g−1 exhibited superior catalytic activity for Suzuki–Miyaura cross-couplings and a catalyst loading of 0.05 mol% is typically sufficient to achieve excellent reaction yields. Notably, the reaction is typically carried out in water without removing atmospheric oxygen. The catalyst is conveniently recycled and remains highly active

  在这里，我们通过固定新型Pd 2+传感器作为介孔二氧化硅上的促进剂，报告了一种非均相催化剂（Pd @ FSM）。Pd @ FSM，钯载量高。11毫克克-1铃木-宫浦交叉偶联显示出优异的催化活性，催化剂负载量通常为0.05 mol％，足以实现出色的反应收率。值得注意的是，该反应通常在水中进行而不除去大气中的氧气。该催化剂可方便地循环使用，即使循环使用5次后仍保持高活性。在此过程中，钯从催化剂的固体载体中的损失可以忽略不计。此外，催化剂可以在空气中储存至少三个月而不会损失其催化活性。这项工作提供了一种通过组合材料和荧光传感器来开发非均相钯催化剂的新方法。
• Synthesis of Chiral Imidazolium Salts from a Carbohydrate and Their Application in Pd-Catalyzed Suzuki–Miyaura Reaction
  作者：Zhonggao Zhou、Jiabin Qiu、Lifang Xie、Fan Du、Guohai Xu、Yongrong Xie、Qidan Ling

  DOI：10.1007/s10562-014-1323-4

  日期：2014.11

  1-(acetylated glucopyranosyl)-3-substituted-imidazolium salts [3-substitute = n-butyl (1a), 3-bromopropyl (1b), 2-chloromethyl benzyl (1c), and 4-chloromethyl benzyl (1d)] have been synthesized. Preliminary catalytic studies show that these imidazolinium salts are remarkably efficient in Pd-catalyzed Suzuki–Miyaura reaction. Functionalized aryl boronic acids reaction with aryl halides (including aryl iodides, aryl

  一系列手性 1-（乙酰化吡喃葡萄糖基）-3-取代的咪唑鎓盐 [3-取代物 = 正丁基 (1a)、3-溴丙基 (1b)、2-氯甲基苄基 (1c) 和 4-氯甲基苄基 ( 1d)] 已经合成。初步催化研究表明，这些咪唑啉盐在 Pd 催化的 Suzuki-Miyaura 反应中非常有效。官能化芳基硼酸与芳基卤化物（包括芳基碘化物、芳基溴化物和活化的芳基氯化物）在环境友好条件（乙醇水溶液和环境条件）下反应。优异的分离收率表明，庞大的碳水化合物单元有望用于构建高活性过渡金属催化剂。图形摘要合成了四种 C-1 键合的含糖手性咪唑盐 1a-d，它们在 Pd 催化的 Suzuki 反应中均表现出优异的催化活性。Pd/1a 对于官能化的芳基硼酸与芳基卤化物（包括活化的芳基氯化物）在空气中的乙醇水溶液中的偶联最为有效。