1-氟-3-(3-甲氧基苯基)苯 | 80254-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-氟-3-(3-甲氧基苯基)苯
• 英文名称: 3'-fluoro-3-methoxybiphenyl
• 英文别名: 3-fluoro-3'-methoxybiphenyl；1-fluoro-3-(3-methoxyphenyl)benzene
• CAS: 80254-68-8
• 化学式: C₁₃H₁₁FO
• 分子量: 202.228
• InChiKey: YRAKETYYOXEFJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-氟-3-(3-甲氧基苯基)苯 在 氢碘酸 作用下， 反应 2.0h， 以97%的产率得到3'-fluorobiphenyl-3-ol
  参考文献：
  名称：

  Cyclohexylcarbamic Acid 3‘- or 4‘-Substituted Biphenyl-3-yl Esters as Fatty Acid Amide Hydrolase Inhibitors:  Synthesis, Quantitative Structure−Activity Relationships, and Molecular Modeling Studies

  摘要：

  Fatty acid amide hydrolase (FAAH) is a promising target for modulating endocannabinoid and fatty acid ethanolamide signaling, which may have important therapeutic potential. We recently described a new class of O-arylcarbamate inhibitors of FAAH, including the cyclohexylcarbamic acid biphenyl-3-yl ester URB524 (half-maximal inhibitory concentration, IC50 = 63 nM), which have significant anxiolytic-like properties in rats. In the present study, by introducing a selected group of substituents at the meta and para positions of the distal phenyl ring of URB524, we have characterized structure-activity profiles for this series of compounds and shown that introduction of small polar groups in the meta position greatly improves inhibitory potency. Most potent in the series was the m-carbamoyl derivative URB597 (4i, IC50 = 4.6 nM). Furthermore, quantitative structure-activity relationship (QSAR) analysis of an extended set of meta-substituted derivatives revealed a negative correlation between potency and lipophilicity and suggested that small-sized substituents may undertake polar interactions with the binding pocket of the enzyme. Docking studies and molecular dynamics simulations, using the crystal structure of FAAH, indicated that the O-biphenyl scaffold of the carbamate inhibitors can be accommodated within a lipophilic region of the substrate-binding site, where their folded shape mimics the initial 10-12 carbon atoms of the arachidonyl moiety of anandamide (a natural FAAH substrate) and methyl arachidonyl fluorophosphonate (a nonselective FAAH inhibitor). Moreover, substituents at the meta position of the distal. phenyl ring can form hydrogen bonds with atoms located on the polar section of a narrow channel pointing toward the membrane-associated side of the enzyme. The structure-activity characterization reported here should help optimize the pharmacodynamic and pharmacokinetic properties of this class of compounds.

  DOI：

  10.1021/jm031140x
• 作为产物：
  描述：

  1,3-二氟苯 、 (3-methoxyphenyl)magnesium bromide 在 titanium(IV) tetraethanolate 、 N,N-二甲基丙烯基脲 、 cobalt(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-氟-3-(3-甲氧基苯基)苯
  参考文献：
  名称：

  在没有磷化氢或NHC配体的情况下，通过CF键活化钴催化的联芳基偶联

  摘要：

  描述了在膦或无NHC的条件下通过CF裂解产生的高度通用的选择性Co催化联芳基偶合。在CoCl 2 / DMPU的催化下，包括未活化的氟化物以及具有敏感功能的芳基氟化物在内的各种芳基氟化物都可以与各种Ti（OEt）4介导的芳基格利雅试剂进行高选择性的偶联。重要的是，还可以实现两种类型的氟之间的选择性CF键活化偶联（二氟芳族化合物和两个不同的偶联配偶体），并且在存在CCl或CBr键的情况下也可以实现。

  DOI：

  10.1021/acs.joc.6b02354

文献信息

• Air-Stable and Catalytically Active Phosphinous Acid Transition-Metal Complexes
  作者：Boris Kurscheid、Lhoussaine Belkoura、Berthold Hoge

  DOI：10.1021/om200697u

  日期：2012.2.27

  Secondary phosphane oxides R2P(O)H are most frequently used as preligands for phosphinous acid R2POH (R = alkyl, aryl) transition-metal complexes, which are very efficient catalysts for cross-coupling reactions. To investigate the influence of electron-deficient substituents on the catalytic activity, the coordination properties of bis(trifluoromethyl)-, bis(pentafluoroethyl)-, and bis[2,4-bis(tri

  仲膦氧化物R 2 P（O）H最常用作次膦酸R 2的预配体POH（R ​​=烷基，芳基）过渡金属络合物，是交叉偶联反应非常有效的催化剂。为了研究缺电子取代基对催化活性，双（三氟甲基）-，双（五氟乙基）-和双[2,4-双（三氟甲基）苯基]次膦酸对催化相关金属的配位性能的影响，例如钯和铂。新型次膦酸钯配合物在Heck和Suzuki交叉偶联反应中显示出高催化活性。由于这些过程对反应条件的强烈依赖，因此进行了以1-溴-3-氟苯和苯基硼酸为模型反应物的系统溶剂和碱的筛选。最有效的溶剂/碱系统由2-丙醇和磷酸钾组成，在室温下放置20 h后，催化剂的负载量为0.01 mol％的钯时，可提供完全转化率和TON约为10000。在室温下20小时后，仅0.004mol％钯的催化剂负载仍导致几乎完全转化。在催化反应过程中，形成相应的次膦酸R观察到2 P（O）OH。进一步的研究得出结论，钯纳米颗粒代表了催化活性物质。
• Palladium-catalyzed Suzuki–Miyaura coupling of aryl sulfamates with arylboronic acids
  作者：Zhan-Yong Wang、Qin-Na Ma、Ren-Hao Li、Li-Xiong Shao

  DOI：10.1039/c3ob41382a

  日期：——

  showed efficient catalytic activity toward the Suzuki–Miyaura coupling of aryl sulfamates with arylboronic acids or potassium phenyltrifluoroborate, giving the expected coupling products in good to high yields. It should be noted that this is the first example so far of the phosphine-free, NHC–Pd(II) complexes catalyzed Suzuki–Miyaura coupling of aryl sulfamates with arylboronic acids.

  现成的NHC-Pd（II）-Mp配合物2对芳基氨基磺酸与芳基硼酸或苯基三氟硼酸钾的Suzuki-Miyaura偶联显示出有效的催化活性，从而以高至高收率提供了预期的偶联产物。应当指出，这是迄今为止不含膦的NHC-Pd（II）配合物催化氨基磺酸芳基磺酸盐与芳基硼酸的Suzuki-Miyaura偶联反应的第一个例子。
• Medicament for treatment of liver cancer
  申请人：Zender Lars

  公开号：US10441577B2

  公开（公告）日：2019-10-15

  The invention provides a pharmaceutical composition comprising Sorafenib in combination with an inhibitor of a specific kinase inhibitor as a medicament for the treatment or prevention of liver cancer.

  本发明提供了一种药物组合物，该组合物由索拉非尼与一种特异性激酶抑制剂组合而成，作为治疗或预防肝癌的药物。
• 10.1039/d4sc01704h
  作者：Mkrtchyan, Satenik、Jakubczyk, Michał、Sarfaraz, Sehrish、Ayub, Khurshid、Iaroshenko, Viktor O.

  DOI：10.1039/d4sc01704h

  日期：——

  nucleophiles under mechanochemical conditions. Conversion of phenolic hydroxy groups without derivatization is important for late-stage modifications of pharmaceuticals and in the context of lignin-material processing. We present a one-step, Ru-catalyzed cross-coupling of phenols with boronic acids, aryl trialkoxysilanes and potassium benzoyltrifluoroborates under mechano-chemical conditions. The protocol

  Ru 催化剂对苯酚的活化使得生成的 η 5 -苯氧配合物能够在机械化学条件下选择性地与各种亲核试剂发生反应。无需衍生化即可转化酚羟基对于药物的后期修饰和木质素材料加工非常重要。我们提出了一种在机械化学条件下，钌催化的苯酚与硼酸、芳基三烷氧基硅烷和苯甲酰基三氟硼酸钾的一步交叉偶联反应。该方案接受多种起始材料，并允许以优异的产率进行克级合成。所开发的方法构成了已知方法的非常有趣且限制浪费的替代方案。
• F-NMR-spectroscopy for the identification of photo products generated from aromatic iodo compounds—IV
  作者：J. Kelm、K. Strauss

  DOI：10.1016/0584-8539(81)80068-2

  日期：1981.1