2-[2-(4-methoxyphenyl)]phenylpyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-(4-methoxyphenyl)]phenylpyridine
• 英文别名: 2-(4'-methoxy-[1,1'-biphenyl]-2-yl)pyridine；2-(4'-methoxybiphenyl-2-yl)pyridine；2-(4’-methoxybiphenyl-2-yl)pyridine；2-[2-(4-Methoxyphenyl)phenyl]pyridine
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: SZNCZSHIVWZRLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(4-methoxyphenyl)]phenylpyridine 在 氢化钾 作用下， 以 甲苯 为溶剂， 以36 %的产率得到
  参考文献：
  名称：

  2-苯基吡啶逐步C-H芳基化还原环化脱氢合成二苯并[f,h]喹啉

  摘要：

  介绍了一种通过逐步钌催化的 C-H 芳基化和钾介导的还原性环化脱氢从 2-苯基吡啶和芳基溴化物合成二苯并 [f, h] 喹啉及其衍生物的方法。一种二苯并[ f , h ] 喹啉衍生物被用作双齿配体来制备环金属化的钌络合物。通过单晶 X 射线结构分析表征了两种二苯并 [ f , h ] 喹啉化合物和钌络合物。

  DOI：

  10.1055/a-2069-4269
• 作为产物：
  描述：

  三正丁基2-吡啶基锌 在 bis(1,5-cyclooctadiene)nickel (0) 、 四(三苯基膦)钯 、 cesium fluoride 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 2-[2-(4-methoxyphenyl)]phenylpyridine
  参考文献：
  名称：

  Nickel-Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides

  摘要：

  Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.

  DOI：

  10.1021/ja207759e

文献信息

• Iron catalyzed oxidative assembly of N-heteroaryl and aryl metal reagents using oxygen as an oxidant
  作者：Kun Ming Liu、Lian Yan Liao、Xin Fang Duan

  DOI：10.1039/c4cc08494b

  日期：——

  An equivalent amount of N-heteroaryl and aryl Grignard or lithium reagents, after mediation by an equivalent of titanate, was facilely coupled to furnish N-heteroaryl-aryl compounds under the catalysis of FeCl3/TMEDA at ambient temperature using oxygen as an oxidant. Most of the common N-heteroaryls were all good candidates, and thus provided a general, green and pratical protocol for the flexible

  在等量的钛酸酯介导之后，在FeCl3 / TMEDA的催化下，在室温下使用氧气作为氧化剂，将等量的N-杂芳基和芳基格氏试剂或锂试剂轻松偶联以提供N-杂芳基-芳基化合物。大多数常见的N-杂芳基都是很好的候选物，因此为各种N-杂芳基-芳基结构的灵活构建提供了通用，绿色和实用的方案。
• Deliberately Losing Control of C−H Activation Processes in the Design of Small‐Molecule‐Fragment Arrays Targeting Peroxisomal Metabolism
  作者：Raysa Khan Tareque、Storm Hassell‐Hart、Tobias Krojer、Anthony Bradley、Srikannathasan Velupillai、Romain Talon、Michael Fairhead、Iain J. Day、Kamlesh Bala、Robert Felix、Paul D. Kemmitt、Paul Brennan、Frank Delft、Laura Díaz Sáez、Kilian Huber、John Spencer

  DOI：10.1002/cmdc.202000543

  日期：2020.12.15

  Combined photochemical arylation, “nuisance effect” (SNAr) reaction sequences have been employed in the design of small arrays for immediate deployment in medium‐throughput X‐ray protein–ligand structure determination. Reactions were deliberately allowed to run “out of control” in terms of selectivity; for example the ortho‐arylation of 2‐phenylpyridine gave five products resulting from mono‐ and bisarylations

  组合光化学芳基化、“滋扰效应”（ SN Ar）反应序列已被用于设计小型阵列，以便立即部署在中等通量 X 射线蛋白质-配体结构测定中。故意让反应在选择性方面“失控”；例如，2-苯基吡啶的邻位芳基化得到单芳基化和双芳基化与SNA Ar 工艺相结合的五种产物。结果，已经鉴定出许多针对 NUDT7（一种关键的过氧化物酶体 CoA 酯水解酶）的晶体学命中。
• Bulky Phosphane Ligand for Monoselective Ruthenium-Catalyzed, Directed o-C–H Arylation with Challenging Aryl Chlorides
  作者：Fuk-Yee Kwong、Eric Kantchev、You-Gui Li、Zhen-Yu Wang、Ya-Ling Zou、Chau-Ming So、Hua-Li Qin

  DOI：10.1055/s-0036-1588635

  日期：——

  more economically attractive but usually much more difficult as substrates in metal-mediated couplings than the corresponding bromides and iodides. A catalyst prepared from a bulky (biaryl)diphenyl phosphane and a common ruthenium source (1:1) mediates selective direct monoarylations of arenes bearing 2-pyridyl and related ortho-directing groups in good yields. Sequential arylations to heterodiarylated

  与相应的溴化物和碘化物相比，官能化芳基氯化物在经济上更具吸引力，但通常更难作为金属介导偶联的底物。由庞大的（联芳基）二苯基膦和常见的钌源 (1:1) 制备的催化剂以良好的收率介导带有 2-吡啶基和相关邻位导向基团的芳烃的选择性直接单芳基化。对杂二芳基化产物的连续芳基化也以令人满意的产率进行。
• Ruthenium-Catalyzed Direct C–H Bond Arylations of Heteroarenes
  作者：Lutz Ackermann、Alexander V. Lygin

  DOI：10.1021/ol2010648

  日期：2011.7.1

  Ruthenium-catalyzed C–H bond arylations of indoles, thiophenes, and pyrroles were accomplished in a highly chemo- and site-selective manner through the use of removable directing groups.

  钌催化的吲哚，噻吩和吡咯的C H键芳基化是通过使用可移动的导向基团以高度化学和位点选择性的方式完成的。
• Solvent and Base in One: Tetra-<i>n</i> -butylammonium Acetate as a Multi-Purpose Ionic Liquid Medium for Ru-Catalyzed Directed Mono- and Di-<i>o</i> -C-H Arylation Reactions
  作者：Ya-Ling Zou、Zhen-Yu Wang、Yin-Mao Feng、You-Gui Li、Eric Assen B. Kantchev

  DOI：10.1002/ejoc.201701022

  日期：2017.11.16

  Bu4NOAc can be a multi-purpose medium for a Ru-catalyzed directed o-C–H arylation reaction with functionalized aryl bromides. Acetate plays the role of base and Bu4N salts (excess acetate and side product bromide) behave as ionic liquids. The medium is compatible with both RuCl3·xH2O (major product: di-arylation) and [RuCl2(p-cymene)]2/(p-Tol)3P catalytic systems (major product: mono-arylation).

  Bu 4 NOAc可以是多官能团介质，用于Ru催化的与官能化芳基溴化物进行的定向o -C–H芳基化反应。乙酸盐起碱的作用，Bu 4 N盐（过量的乙酸盐和副产物溴化物）起离子液体的作用。该介质与RuCl 3 · x H 2 O（主要产物：二芳基化）和[RuCl 2（p- cymene）] 2 /（p -Tol）3 P催化系统兼容（主要产物：单芳基化） 。