2-(4-methoxyphenyl)-5-phenylpyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-methoxyphenyl)-5-phenylpyridine
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: IFHABFINXPFJNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

• 作为产物：
  描述：

  2,5-二溴吡啶 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2-(4-methoxyphenyl)-5-phenylpyridine
  参考文献：
  名称：

  Disubstituted Pyridines:  The Double-Coupling Approach

  摘要：

  A one-pot procedure leading to disubstituted pyridines from the starting dibromopyridines is described. Key features include the ability to couple a range of aryl and even alkenylboronic acids at the 2,3 and/or 2,5 positions with excellent regiocontrol under a standard set of conditions. Further, isolated yields are greatly improved by the use of neutral alumina in place of silica for product purification. Finally, the intrinsic electronic bias of the pyridine ring can be overcome by using a bromoiodopyridine.

  DOI：

  10.1021/jo701709a

文献信息

• Highly Selective Room-Temperature Suzuki–Miyaura Coupling of Bromo-2-sulfonyloxypyridines for Unsymmetrical Diarylpyridines
  作者：Young-Kyo Jeon、Jae-Yeon Lee、Seo-Eun Kim、Won-Suk Kim

  DOI：10.1021/acs.joc.0c00793

  日期：2020.6.5

  A new and mild synthetic approach has been developed for the synthesis of pharmaceutically important unsymmetrical diarylpyridines via chemoselective Suzuki–Miyaura coupling reactions of bromo-2-sulfonyloxypyridines. Most reactions allow for facile access to aryl-2-sulfonyloxypyridines at room temperature in yields of 5–99% with excellent chemoselectivity in the presence of Pd(OAc)2 (2.0 mol %) and

  已经开发出一种新的，温和的合成方法，用于通过溴-2-磺酰氧基吡啶的化学选择性Suzuki-Miyaura偶联反应合成药学上重要的不对称二芳基吡啶。在室温下，在Pd（OAc）2（2.0 mol％）和Ad 2存在的情况下，大多数反应均可轻松获得芳基-2-磺酰氧基吡啶，产率为5–99％，且具有出色的化学选择性。BnP（2.4mol％）。获得的单芳基吡啶衍生物中剩余的甲苯磺酰基或三氟甲基的第二芳基化成功地完成了不对称的2,3-，2,4-，2,5-和2,6-二芳基吡啶衍生物的合成。此外，完成了从溴-2-磺酰氧基吡啶开始的不对称二芳基吡啶的一锅合成，以证明实际的便利性。最后，用这种方法，由相应的溴-2-羟基吡啶成功地合成了一种抗菌剂，一种拓扑异构酶抑制剂和一种非甾体抗炎药依托考昔，其总收率分别为80％，86％和49％。
• An efficient water-soluble surfactant-type palladium catalyst for Suzuki cross-coupling reactions in pure water at room temperature
  作者：Pei Qiu、Jing Yang Zhao、Xu Shi、Xin Hong Duan

  DOI：10.1039/c6nj00377j

  日期：——

  An in situ-generated Pd catalyst with a bidentate phosphine-type zwitterionic surfactant as a ligand showed high catalytic activity in the Suzuki reactions.

  一个以双齿膦型带电离表面活性剂为配体的原位生成的Pd催化剂在Suzuki反应中表现出高催化活性。
• A Unique Synthetic Method for Pyridine-Ring Containing Ter-, Quater- and Quinquearyl and Vinylogues by Thermolysis of 2,2-Dichlorocyclopropylmethyleneamines
  作者：Shinzo Kagabu、Shinji Mizoguchi

  DOI：10.1055/s-1996-4220

  日期：1996.3

  Teraryls, quateraryls, and quinquearyls composed of a pyridine ring in the segment and their vinylogues were prepared directly by thermal rearrangement of N-(hetero)arylmethyl-2,2-dichloro-1-substituted phenylcyclopropylmethyleneamines in modest to good yields.

  通过对 N-（杂）芳基甲基-2,2-二氯-1-取代苯基环丙基亚甲基胺进行热重排，直接制备了在段中由一个吡啶环组成的三元、四元和五元及其乙烯基对映体，收率从一般到良好。
• Thermal Rearrangement of<i>N</i>-Alkyl-, and<i>N</i>-Aryl-(2,2-dihalo-1-phenylcyclopropyl)methyleneamines to 1-Alkyl-, and 1-Aryl-2 (or 3)-halo-4-phenylpyrroles
  作者：Shinzo Kagabu、Hideaki Tsuji、Itsumi Kawai、Hitomi Ozeki

  DOI：10.1246/bcsj.68.341

  日期：1995.1

  1,3-bond cleavage. The ionic mechanism involving a heterolytic dissociation of chlorine atom under 1,3-bond scission of the cyclopropane ring is proposed for the rearrangement to 3-chloropyrroles, while a homolytic cleavage pathway is proposed for 3-fluoropyrroles. The present thermolysis supplies a unique preparative tool for 2-, and 3-halo-4-phenylpyrrole derivatives.

  Nt-烷基-和N-芳基-(2,2-二氯环丙基)亚甲基胺的热解直接产生1-t-烷基和1-芳基-3-氯吡咯作为主要产物以及少量的2-氯异构体。在极性溶剂中，向 3-氯吡咯的转化得到增强。但是碱性添加剂将热重排引导到环丙烷环的 1,2-键断裂中，从而产生 2-氯吡咯。另一方面，（二氟环丙基）亚甲基胺在 1,3-键断裂下仅被热解为 3-氟吡咯。提出了在环丙烷环的 1,3-键断裂下氯原子异裂解离的离子机制，用于重排为 3-氯吡咯，而为 3-氟吡咯提出了均裂途径。
• Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis
  作者：Maddali L.N. Rao、Ritesh J. Dhanorkar

  DOI：10.1016/j.tet.2014.11.036

  日期：2015.1

  This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines in high yields. The couplings addressed with dihalopyridines have afforded chemo- and regio-selective coupling products. Arylations of 2-chloroquinoline with different triarylbismuth reagents demonstrated fruitful coupling reactivity under the established conditions. This sumptuous study demonstrates the remarkable cross-coupling reactivity of iodo/chloropyridines and chloroquinoline with triarylbismuth reagents. (C) 2014 Elsevier Ltd. All rights reserved.