4-acetyl-4'-(methylthio)<1,1'-biphenyl> | 83085-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-4'-(methylthio)<1,1'-biphenyl>
• 英文别名: 4-acetyl-4'-(methylthio)-1,1'-biphenyl；4-acetyl-4'-(methylthio)biphenyl；4-acetyl-4'-(methylthio)(1,1'-biphenyl)；1-(4'-(Methylthio)-[1,1'-biphenyl]-4-yl)ethan-1-one；1-[4-(4-methylsulfanylphenyl)phenyl]ethanone
• CAS: 83085-94-3
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: ORXCVHABGOLGPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetyl-4'-(methylthio)<1,1'-biphenyl> 在 sodium hydroxide 、 sodium methylate 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 反应 2.5h， 生成 4-[(4'-methylthio-1,1'-biphenyl)-4-yl]-2,4-dioxo-1-butanoic acid
  参考文献：
  名称：

  Inhibitors of glycolic acid oxidase. 4-Substituted-2,4-dioxobutanoic acid derivatives

  摘要：

  Fourteen new 4-substituted 2,4-dioxobutanoic acids have been synthesized. These compounds, all of which contain lipophilic 4-substituents, are potent inhibitors in vitro of porcine liver glycolic acid oxidase. The I50 value of the two most potent representatives, 4-(4'-bromo[1,1'-biphenyl]-4-yl)-2, 4-dioxobutanoic acid (8) and 4-[4'-[[(3,4-dihydro-3-hydroxy-2H-1, 5-benzodioxepin-3-yl)methyl]thio][1,1'-biphenyl]-4-yl]-2, 4-dioxobutanoic acid (13) is 6 X 10(-8)M.

  DOI：

  10.1021/jm00362a020
• 作为产物：
  描述：

  1-[4-(4-羟基苯基)苯基]乙酮 在 sodium hydroxide 、 sodium hydride 作用下， 反应 5.0h， 生成 4-acetyl-4'-(methylthio)<1,1'-biphenyl>
  参考文献：
  名称：

  Inhibitors of glycolic acid oxidase. 4-Substituted-2,4-dioxobutanoic acid derivatives

  摘要：

  Fourteen new 4-substituted 2,4-dioxobutanoic acids have been synthesized. These compounds, all of which contain lipophilic 4-substituents, are potent inhibitors in vitro of porcine liver glycolic acid oxidase. The I50 value of the two most potent representatives, 4-(4'-bromo[1,1'-biphenyl]-4-yl)-2, 4-dioxobutanoic acid (8) and 4-[4'-[[(3,4-dihydro-3-hydroxy-2H-1, 5-benzodioxepin-3-yl)methyl]thio][1,1'-biphenyl]-4-yl]-2, 4-dioxobutanoic acid (13) is 6 X 10(-8)M.

  DOI：

  10.1021/jm00362a020

文献信息

• Polyvinylpyridine, a Versatile Solid Phase for Coordinative Immobilisation of Palladium Precatalysts - Applications in Suzuki-Miyaura Reactions
  作者：Andreas Kirschning、Wladimir Solodenko、Klaas Mennecke、Carla Vogt、Susan Gruhl

  DOI：10.1055/s-2006-942370

  日期：2006.6

  The immobilisation of an oxime-based palladacycle on polyvinylpyridine (PVP) resin affords a reusable, air, moisture and thermally stable palladium precatalyst which exerts high activity in Suzuki-Miyaura reactions both in batch as well as continuous-flow processes. Evidence is presented which shows that, besides serving as an anchor for the precatalyst, PVP also acts as a scavenger for Pd particles present in solution.

  将基于肟的钯配合物固定在聚乙烯吡啶（PVP）树脂上，制备出一种可重复使用、对空气、湿气和热稳定的钯前催化剂，在Suzuki-Miyaura反应中，无论是在批次反应还是连续流动过程中，都表现出高活性。有证据表明，除了作为前催化剂的锚点外，PVP还充当溶液中钯粒子的清除剂。
• Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions
  作者：Klaas Mennecke、Andreas Kirschning

  DOI：10.3762/bjoc.5.21

  日期：——

  The preparation of monolithic polyionic supports which serve as efficient heterogeneous supports for palladium(0) nanoparticles is described. These functionalized polymers were incorporated inside a flow reactor and employed in Suzuki–Miyaura and Heck cross couplings under continuous flow conditions.

  单体多离子支撑材料的制备，这些材料可作为钯(0)纳米颗粒的高效异质支撑，已经被描述。这些功能化聚合物被纳入流动反应器中，并在连续流动条件下用于Suzuki–Miyaura和Heck交叉偶联反应。
• Carbon-Carbon Cross-Coupling Reactions under Continuous Flow Conditions Using Poly(vinylpyridine) Doped with Palladium
  作者：Andreas Kirschning、Klaas Mennecke、Wladimir Solodenko

  DOI：10.1055/s-2008-1072579

  日期：2008.5

  as Raschig rings or placed within the PASSflow TM microreactor affords technical devices that are well suited for performing palladium-catalyzed carbon-carbon cross-coupling reactions in the flow-through mode. Reusability of the immobilized precatalyst as well as applications in the microwave field were investigated. Experiments with thiol- and pyridine-based scavengers were carried out, which revealed

  将肟基钯环配位固定到形状为拉西环或放置在 PASSflow TM 微反应器中的聚（乙烯基吡啶）/玻璃复合材料上，提供了非常适合在流动中进行钯催化的碳-碳交叉偶联反应的技术设备-直通模式。研究了固定化预催化剂的可重复使用性以及在微波领域的应用。进行了基于硫醇和吡啶的清除剂的实验，结果表明活性钯物质很可能由性质未知的纳米颗粒组成，并且聚（乙烯基吡啶）载体对这些颗粒具有清除性能。
• Microwave-Assisted Suzuki-Miyaura Reactions with an Insoluble Pyridine-Aldoxime Pd-Catalyst
  作者：Andreas Kirschning、Wladimir Solodenko、Uwe Schön、Josef Messinger、Anja Glinschert

  DOI：10.1055/s-2004-829546

  日期：——

  The preparation of a solid Pd(II)-precatalyst and its use in microwave-assisted Suzuki-Miyaura reactions in water is described. The precatalyst is obtained by treatment of 4-pyridine-aldoxime with Na2PdCl4 and is insoluble in organic solvents as well as in water. Its robustness under microwave conditions and its insolubility allows simple reuse in ‘teabags’.

  报道了固体Pd(II)前催化剂的制备及其在水中的微波辅助Suzuki-Miyaura反应中的应用。该前催化剂是通过4-吡啶醛肟与Na2PdCl4处理获得的，在有机溶剂和水中的溶解性都很差。它在微波条件下的稳定性和不溶性使其能够简单地在“茶袋”中重复使用。
• Design, synthesis and biological evaluation of 5-hydroxy, 5-substituted-pyrimidine-2,4,6-triones as potent inhibitors of gelatinases MMP-2 and MMP-9
  作者：Orazio Nicolotti、Marco Catto、Ilenia Giangreco、Maria Barletta、Francesco Leonetti、Angela Stefanachi、Leonardo Pisani、Saverio Cellamare、Paolo Tortorella、Fulvio Loiodice、Angelo Carotti

  DOI：10.1016/j.ejmech.2012.09.036

  日期：2012.12

  rational design led to the discovery of highly potent MMP inhibitors. In particular, biphenyl derivatives bearing at the para position COCH3 and OCF3 substituents permitted to inhibit gelatinases MMP-2 and MMP-9, with IC50 values as low as 30 nM and 21 nM, respectively, whereas the introduction at the same position of the bulkier SO2CH3 group afforded a potent collagenase MMP-8 inhibitor with an IC50

  基质金属蛋白酶（MMP）是有吸引力的生物学靶标，在许多生理病理学过程中起着关键作用，例如细胞外基质蛋白的降解，细胞表面受体的释放和裂解，肿瘤进展，体内稳态调节和先天免疫。合理设计，制备和测试了一系列5-羟基，5-取代的嘧啶-2,4,6-三酮，作为明胶酶MMP-2和MMP-9和胶原酶MMP-8的抑制剂。一方面，代表此类化合物的典型特征的5-羟基的存在确保了诱人的药代动力学特征，而另一方面，通过酮亚甲基连接基连接至位置5的适当取代的联芳基分子片段则确保了良好的药代动力学特性。 S 1的深部区域的相互作用'酶亚位点。这种合理的设计导致了高效MMP抑制剂的发现。特别是，在对位带有COCH 3和OCF 3取代基的联苯衍生物可以抑制明胶酶MMP-2和MMP-9，IC 50值分别低至30 nM和21 nM，而引入相同位置较大的SO 2 CH 3基团提供了有效的胶原酶MMP-8抑制剂，IC 50值等于66