3-([1,1'-biphenyl]-4-yl)pyridine | 93324-68-6

• 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: 3-([1,1'-biphenyl]-4-yl)pyridine
• 英文别名: 3-([1,1’-biphenyl]-4-yl)pyridine；3-[1,1'-Biphenyl]-4-ylpyridine；3-(4-phenylphenyl)pyridine
• CAS: 93324-68-6
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: OIWJBXODTRCYHF-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  420.0±14.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-([1,1'-biphenyl]-4-yl)pyridine 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 60.0~70.0 ℃ 、275.8 kPa 条件下， 反应 36.0h， 生成 3-([1,1'-biphenyl]-4-yl)-1-(cyclopentylmethyl)piperidine
  参考文献：
  名称：

  COMPOUNDS FOR THE MODULATION OF PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9)

  摘要：

  本公开涉及新型化合物，能够结合到PCSK9，从而调节PCSK9的生物活性。还提供了包含这些化合物的组合物，制备这些化合物的方法，以及使用这些化合物治疗与PCSK9相关的疾病和病症的方法。

  公开号：

  US20220193058A1
• 作为产物：
  描述：

  3-(三甲基锡烷基)-吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 氢氧化钾 、 copper(l) iodide 、 正丁基锂 、 四甲基乙二胺 、 三苯胂 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 3-([1,1'-biphenyl]-4-yl)pyridine
  参考文献：
  名称：

  Self-Assembly of 3-[4‘-(Diethylboryl)phenyl]pyridine and 3-[3‘-(Diethylboryl)phenyl]pyridine:  Synthesis, Structural Features, and Stability in Solution

  摘要：

  The self-assembly of 3-[4'-(diethylboryl)phenyl]pyridine (3) and 3-[3'-(diethylboryl)phenyl]pyridine (4) was investigated by H-1 and B-11 NMR spectroscopies and vapor pressure osmometry. It can be seen that in solution 3 affords an equilibrium mixture of oligomers including a cyclic trimer as a major component via intermolecular boron-nitrogen coordination bonds, which is supported by temperature-, concentration-, and solvent-dependent behaviors of 3. In contrast, 4 seems to afford a mixture of oligomers including a cyclic dimer in solution. Judging from the low coalescence temperature in variable-temperature NMR in toluene-d(8) and easy scrambling with the corresponding 3-[(diethylboryl)pheny]-5-methoxypyridines at ambient temperature, it is concluded that the intermolecular boron-nitrogen coordination bonds made by 3 or 4 are weaker than those formed by 3-(diethylboryl)pyridine (1) or 2-(diethylboryl)-5-methylpyridine (2). Poor thermal stability was supported by electrospray mass spectrometry and structural analyses utilizing a semi-empirical molecular orbital calculation AM1. It is noted that in the assembly of 4 there is a tendency to maintain high tetrahedral character at the boron atom in the complex at the expense of strain energy. Thus, these features of 3 and 4 in solution are in marked contrast to those of 1 and 2.

  DOI：

  10.1021/jo981632v

文献信息

• Air-Stable and Highly Active Dendritic Phosphine Oxide- Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon-Carbon Bond Formation and Hydrogenation Reactions
  作者：Lei Wu、Zhi-Wei Li、Feng Zhang、Yan-Mei He、Qing-Hua Fan

  DOI：10.1002/adsc.200700441

  日期：2008.4.7

  compared with the commonly used homogeneous catalyst tetrakis(triphenylphosphine)palladium [Pd(PPh3)4]. In addition, the results obtained from the bulky dendritic substrate suggest that the Pd nanoparticles might act as reservoir of catalytically active species, and that the reaction is actually catalyzed by the soluble Pd(0) and/or Pd(II) species leached from the nanoparticle surface.

  在膦树状大分子配体存在下，使用氢在四氢呋喃中还原双（乙酰丙酮）钯[Pd（acac）2 ]，形成树状大分子稳定的钯纳米颗粒。通过TEM，31 P NMR和31表征所得的Pd纳米颗粒P MAS NMR。结果表明，树枝状膦配体被氧化为氧化膦。这些树状聚合物稳定的Pd纳米颗粒被证明是Suzuki和Stille偶联反应和氢化的有效催化剂。树状楔用作稳定剂以防止纳米颗粒聚集，并且用作促进Pd催化剂的分离和/或再循环的载体。在铃木偶联反应的情况下，与常用的均相催化剂四（三苯基膦）钯[Pd（PPh 3）4相比，这些Pd纳米颗粒显示出高催化效率（TON高达65,000）和空气稳定性。]。此外，从庞大的树突状基质获得的结果表明，Pd纳米颗粒可能充当催化活性物质的储存库，并且该反应实际上是由从水中浸出的可溶性Pd（0）和/或Pd（II）物质催化的。纳米颗粒表面。
• Nickel-Catalyzed Decarbonylative Cou­pling of Aryl Esters and Arylboronic Acids
  作者：Nicole A. LaBerge、Jennifer A. Love

  DOI：10.1002/ejoc.201500630

  日期：2015.9

  accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki–Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals

  在由 Ni(cod)2 和 PCy3 组成的经济实惠的催化剂体系催化下，在 Suzuki-Miyaura 型脱羰交叉偶联中将芳基和杂芳基酯与硼酸偶联，可以获得多种功能化的联芳基化合物。该方法可以耐受各种官能团，并为目前工业中使用钯催化获得此类双（杂）芳基提供了一种有吸引力的替代方案，但也揭示了与交叉偶联化学中酯的镍催化相关的挑战。
• Pd-catalyzed C3-selective arylation of pyridines with phenyl tosylates
  作者：Fenglin Dai、Qingwen Gui、Jidan Liu、Zhiyong Yang、Xiang Chen、Ruqing Guo、Ze Tan

  DOI：10.1039/c3cc41066h

  日期：——

  We have discovered that phenyl tosylates can be used to arylate pyridines at the C3-position using a Pd(OAc)2–1,10-phenanthroline catalyst system. We also discovered that the reaction of 4-methylpyridine with naphthyl tosylates occurred on the methyl group instead of at the C3-position.

  我们发现，苯基磺酰酯可以在C3位点上使用Pd(OAc)2–1,10-菲啰啉催化体系对吡啶进行芳基化。我们还发现，4-甲基吡啶与萘基磺酰酯的反应发生在甲基上，而不是在C3位点。
• Intramolecular carbolithiation of <i>N</i>-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines – application to a formal synthesis of sarizotan
  作者：Wafa Gati、Mohamed M Rammah、Mohamed B Rammah、Gwilherm Evano

  DOI：10.3762/bjoc.8.250

  日期：——

  developed a general synthesis of polysubstituted 1,4-dihydropyridines and pyridines based on a highly regioselective lithiation/6-endo-dig intramolecular carbolithiation from readily available N-allyl-ynamides. This reaction, which has been successfully applied to the formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates

  我们已经开发了一种基于高度区域选择性锂化/6-endo-dig 分子内碳锂化的多取代 1,4-二氢吡啶和吡啶的一般合成方法，该方法来自容易获得的 N-烯丙基-炔酰胺。该反应已成功应用于抗运动障碍剂sarizotan的正式合成，进一步扩展了ynamides在有机合成中的应用，并进一步证明了碳金属化反应的合成效率。
• 4-Position-Selective C–H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds
  作者：Masahiro Nagase、Yoichiro Kuninobu、Motomu Kanai

  DOI：10.1021/jacs.6b01753

  日期：2016.5.18

  The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded

  使用亲核全氟烷基化和全氟芳基化试剂实现了六元杂芳族化合物的第一个 4 位选择性 CH 全氟烷基化和全氟芳基化。区域选择性是通过亲电激活杂芳环来控制的，同时空间阻碍了 2 位，使用空间上庞大的硼烷路易斯酸。反应以良好的收率进行，甚至以克规模进行，并且通过不分离中间体的顺序反应进行。该反应可应用于生物活性化合物的后期三氟甲基化。