1-氟-4-(3-甲氧基苯基)苯 | 10540-43-9

• 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-4-(3-甲氧基苯基)苯
• 英文名称: 4'-fluoro-3-methoxy-1,1'-biphenyl
• 英文别名: 4'-fluoro-3-methoxybiphenyl；4-Fluor-3'-methoxybiphenyl；4-Fluoro-3'-methoxybiphenyl；1-fluoro-4-(3-methoxyphenyl)benzene
• CAS: 10540-43-9
• 化学式: C₁₃H₁₁FO
• 分子量: 202.228
• InChiKey: UTWJYUQVXOJBGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  291.5±15.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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-4-(3-甲氧基苯基)苯 在 氢碘酸 作用下， 反应 3.0h， 以53%的产率得到4'-fluoro-[1,1'-biphenyl]-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：

  3-(4-fluorophenyl)cyclohex-2-enone 在 palladium on activated charcoal sodium hydroxide 作用下， 生成 1-氟-4-(3-甲氧基苯基)苯
  参考文献：
  名称：

  Substituent Effects. VI.^1,2 Fluorine Nuclear Magnetic Resonance Spectra of 3'- and 4'-Substituted 4-Fluorobiphenyls and 3″-Substituted 4-Fluoroterphenyls

  摘要：

  DOI：

  10.1021/ja00966a026

文献信息

• Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
  作者：Arif Music、Andreas N. Baumann、Philipp Spieß、Allan Plantefol、Thomas C. Jagau、Dorian Didier

  DOI：10.1021/jacs.9b12300

  日期：2020.3.4

  scope, scalability and robustness of this unconventional catalyst-free transformation, leading to functional-ized biaryls and ultimately furnishing drug-like small molecules as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental

  我们在此报告了由三氟芳基硼酸钾的配体交换反应制备的不对称四（杂）芳基硼酸盐（TAB）的氧化电偶联促进的多功能、无过渡金属和无添加剂的（杂）芳基-芳基偶联反应。该方法利用电化学氧化的能力，补充了现有的有机硼工具箱。我们展示了这种非常规无催化剂转化的广泛范围、可扩展性和稳健性，导致功能化联芳并最终提供类药物小分子以及天然化合物的后期衍生化。此外，通过量子化学计算和实验研究，观察到的氧化偶联反应的选择性与 TAB 的电子结构有关。
• Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki–Miyaura cross-coupling reaction
  作者：You Chen、Hui Peng、Yun-Xiao Pi、Tong Meng、Ze-Yu Lian、Meng-Qi Yan、Yan Liu、Sheng-Hua Liu、Guang-Ao Yu

  DOI：10.1039/c4ob02436b

  日期：——

  We report the synthesis of 2-(anthracen-9-yl)-1H-inden-3-yl dicyclohexylphosphine and its use in palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction to prepare a variety of symmetrical and unsymmetrical biaryl compounds in excellent yield.

  我们报告了2-（蒽-9-基）-1H-茚满-3-基二环己基膦的合成及其在钯催化的硼化/铃木-宫浦交叉偶联反应中的制备，以制备各种对称和不对称的联芳基化合物。优良的产量。
• N-Methylimidazole functionalized carboxymethycellulose-supported Pd catalyst and its applications in Suzuki cross-coupling reaction
  作者：Yahao Dong、Xiaotian Wu、Xiaofeng Chen、Yuping Wei

  DOI：10.1016/j.carbpol.2016.12.044

  日期：2017.3

  ted palladium nanoparticles (CMC-NHC-Pd) was synthesized and characterized by TEM, SEM, EDX, CP/MAS 13C NMR, FT-IR, TGA, XRD, and XPS analysis. The prepared nanoparticles can be used as an environmentally-friendly and trifunctional catalyst. The well-designed CMC supported palladium nanoparticles catalyst with polydentate ligands is also stable and efficient for Suzuki cross-coupling reactions under

  本文合成了N-甲基咪唑官能化的羧甲基纤维素负载的钯纳米颗粒（CMC-NHC-Pd），并通过TEM，SEM，EDX，CP / MAS 13C NMR，FT-IR，TGA，XRD和XPS分析对其进行了表征。制备的纳米颗粒可以用作环境友好的三官能催化剂。经过精心设计的具有多齿配体的CMC负载的钯纳米粒子催化剂在三官能团俘获位点与钯，-COO-，-OH和N-甲基咪唑的协同作用下，在温和条件下对于Suzuki交叉偶联反应也是稳定有效的。通过几个简单的过滤循环就可以容易地回收该催化剂。这项工作提出了一种可行的三官能催化剂配合物。
• Organic transformations catalyzed by palladium nanoparticles on carbon nanomaterials
  作者：Bhairi Lakshminarayana、Lodi Mahendar、Jhonti Chakraborty、Gedu Satyanarayana、Ch Subrahmanyam

  DOI：10.1007/s12039-018-1449-9

  日期：2018.5

  AbstractAn efficient C–C bond coupling reactions (Suzuki–Miyaura and Glaser) catalyzed by PdO/GO nano-catalyst is presented. In addition, PdO/MWCNT nano-catalyst-mediated domino one-pot synthesis of 2-alkyl/2-aryl benzofurans has been accomplished from 2-iodophenols and terminal alkynes. The formation of benzofurans proceeds through intermolecular Sonogashira reaction followed by intramolecular nucleophilic

  摘要提出了由PdO / GO纳米催化剂催化的有效的C-C键偶联反应（Suzuki-Miyaura和Glaser）。另外，已经由2-碘酚和末端炔烃完成了PdO / MWCNT纳米催化剂介导的2-烷基/ 2-芳基苯并呋喃的多米诺骨牌一锅法合成。苯并呋喃的形成通过分子间的Sonogashira反应进行，然后将内部羟基的分子内亲核加成到炔键上。催化剂PdO / GO已成功重复使用，在5个循环内几乎没有活性损失。 图形概要： 概要：已经开发出一种有效的PdO / GO和PdO / MWCNT纳米催化剂，用于C-C偶联反应，例如Suzuki和Glaser偶联反应，由2-碘苯酚和2-烷基苯甲酸酯形成的2-芳基，2-烷基苯并呋喃的多催化一锅合成。末端炔烃。该方案涉及苯并呋喃衍生物的形成，即Sonogashira反应，然后进行2-乙炔基苯酚环化。
• Towards environmentally friendlier Suzuki–Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes
  作者：Caroline M. Zinser、Katie G. Warren、Rebecca E. Meadows、Fady Nahra、Abdullah M. Al-Majid、Assem Barakat、Mohammad S. Islam、Steven P. Nolan、Catherine S. J. Cazin

  DOI：10.1039/c8gc00860d

  日期：——

  preparation of [NHC·H][Pd(η3-R-allyl)Cl2] complexes is disclosed and represents a facile, atom-economical, environmentally friendly and rapid synthesis. These palladates are immediate synthetic precursors to the well-known [Pd(NHC)(η3-R-allyl)Cl] complexes. Their activation leading to catalytically relevant species has been studied in the Suzuki–Miyaura reaction. The need for an activation step prior

  的制备[NHC·H] [将Pd（η 3 -R烯丙基）氯2 ]配合物公开并代表一个轻便，原子经济，环保及快速合成。这些palladates是直接合成前体的公知的[将Pd（NHC）（η 3-R-烯丙基）Cl]络合物。在Suzuki-Miyaura反应中已经研究了它们的活化导致相关的催化物种。检查了在催化之前是否需要活化步骤。反应范围从官能团耐受性上展示了它的简便性和广度。给电子和吸电子的芳基氯化物和溴化物以及含杂原子和空间位阻的芳基卤化物均有效耦合。催化反应是在乙醇中用弱且便宜的无机碱进行的。