2,3-di-(4-tolyl)pyridine | 181883-10-3

• 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: 2,3-di-(4-tolyl)pyridine
• 英文别名: 2,3-di(p-tolyl)pyridine；Dimethyldiphenylazine；2,3-bis(4-methylphenyl)pyridine
• CAS: 181883-10-3
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: SMARVOBNSZRHSC-UHFFFAOYSA-N

物化性质

• 沸点：
  374.4±11.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,3-di-(4-tolyl)pyridine 在 吡啶 、 三(五氟苯基)硼烷 、 氢气 、 频那醇硼烷 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、3.0 MPa 条件下， 反应 24.0h， 以96%的产率得到C₁₉H₂₃N
  参考文献：
  名称：

  通过硼氢化/氢化级联硼烷催化还原吡啶

  摘要：

  我们已经开发了一种用于 B(C 6 F 5 ) 3催化的吡啶的硼氢化/氢化级联还原的方法。该方法对 2,3-二取代吡啶特别有效，它以高产率和高顺式选择性生成哌啶。机理研究表明，吡啶底物和哌啶产物依次作为碱基与B(C 6 F 5 ) 3合作分裂H 2。该方法的广泛官能团耐受性使其可用于合成一些生物活性分子。

  DOI：

  10.1021/acscatal.1c02876
• 作为产物：
  描述：

  4-甲苯硼酸 在 palladium diacetate 、 2,2'-双(二苯基磷)联苯 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 2,3-di-(4-tolyl)pyridine
  参考文献：
  名称：

  Double-coupling of dibromo arenes with aryltriolborates for synthesis of diaryl-substituted planar frameworks

  摘要：

  A new method for simple and practical synthesis of diaryl-substituted arenes using potassium aryltriolborates was developed. Double-cross-coupling of dibromo arenes with aryltriolborates was carried out in the presence of a palladium catalyst, such as Pd(OAc)(2), Pd(PPh3)(4) or Pd(OAc)(2)/BIPHEP. The use of CuCl (40 mol %) with a palladium catalyst was found to be highly effective to give diaryl-substituted aromatic compounds in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.083

文献信息

• Suzuki Coupling of Heteroaromatic Chlorides Using Highly Electron-Donating ClickPhos Ligands
  作者：Xumu Zhang、Stephen Spinella、Zheng-Hui Guan、Jian Chen

  DOI：10.1055/s-0029-1216942

  日期：2009.9

  Using highly electron-rich monophosphine ligands, Suzuki­ cross-coupling of heteroaromatic chlorides with various boronic­ acids was carried out in high yields. High yields were also often observed when steric heteroaromatic chlorides were employed in Suzuki cross-coupling reactions. Suzuki coupling - ClickPhos - heteroaromatic chlorides - palladium

  使用高度富电子的单膦配体，以高收率进行了杂芳族氯化物与各种硼酸的Suzuki交叉偶联。当在铃木交叉偶联反应中使用空间杂芳族氯化物时，也经常观察到高收率。 铃木偶合-ClickPhos-杂芳族氯化物-钯
• Substituted pyridines from isoxazoles: scope and mechanism
  作者：Seokjoo Lee、Rashmi Jena、Aaron L. Odom

  DOI：10.1039/d2ob00779g

  日期：——

  Treatment of isoxazoles with enamines leads to an inverse electron-demand hetero-Diels–Alder reaction that produces substituted pyridines in the presence of TiCl4(THF)2 and titanium powder. The reaction is highly regioselective with only a single isomer of the product observed by GC/MS and tolerant of many common functional groups. The transformation was examined computationally, and it was found that

  用烯胺处理异恶唑会导致在 TiCl 4 (THF) 2和钛粉存在下产生取代的吡啶的逆电子需求杂狄尔斯-阿尔德反应。该反应具有高度区域选择性，通过 GC/MS 仅观察到产物的单一异构体，并且耐受许多常见的官能团。对转化进行了计算检查，发现 TiCl 4（或类似的路易斯酸）可能起到催化反应的作用。在最初的 [4 + 2]-环加成之后，恶氮杂-[2.2.1]-二环在胺损失之前可能会开环以产生N-氧化物。然后用TiCl 4和钛粉还原后得到吡啶。
• Double-coupling of dibromo arenes with aryltriolborates for synthesis of diaryl-substituted planar frameworks
  作者：Gao-Qiang Li、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1016/j.tet.2011.06.083

  日期：2011.9

  A new method for simple and practical synthesis of diaryl-substituted arenes using potassium aryltriolborates was developed. Double-cross-coupling of dibromo arenes with aryltriolborates was carried out in the presence of a palladium catalyst, such as Pd(OAc)(2), Pd(PPh3)(4) or Pd(OAc)(2)/BIPHEP. The use of CuCl (40 mol %) with a palladium catalyst was found to be highly effective to give diaryl-substituted aromatic compounds in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade
  作者：Zhao-Ying Yang、Heng Luo、Ming Zhang、Xiao-Chen Wang

  DOI：10.1021/acscatal.1c02876

  日期：2021.9.3

  of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B(C6F5)3 to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some

  我们已经开发了一种用于 B(C 6 F 5 ) 3催化的吡啶的硼氢化/氢化级联还原的方法。该方法对 2,3-二取代吡啶特别有效，它以高产率和高顺式选择性生成哌啶。机理研究表明，吡啶底物和哌啶产物依次作为碱基与B(C 6 F 5 ) 3合作分裂H 2。该方法的广泛官能团耐受性使其可用于合成一些生物活性分子。