4-[4-(2-phenylethynyl)phenyl]pyridine | 1352050-07-7

• 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: 4-[4-(2-phenylethynyl)phenyl]pyridine
• 英文别名: 4-(4-(phenylethynyl)phenyl)pyridine
• CAS: 1352050-07-7
• 化学式: C₁₉H₁₃N
• 分子量: 255.319
• InChiKey: CZTIEKSOABIQHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-[4-(2-phenylethynyl)phenyl]pyridine 、 2,3,4,5-tetrakis(4-(4-pyridyl)phenyl)cyclopenta-2,4-dienone 反应 96.0h， 以26%的产率得到1,2,3,4,5-pentakis(4-pyridyl)-hexaphenylbenzene
  参考文献：
  名称：

  Stepwise Effective Molarities in Porphyrin Oligomer Complexes: Preorganization Results in Exceptionally Strong Chelate Cooperativity

  摘要：

  Complexes of zinc porphyrin oligomers with multivalent ligands can be denatured by adding a large excess of a monodentate ligand, such as quinuclidine. We have used denaturation titrations to determine the stabilities of the complexes of a cyclic zinc-porphyrin hexamer with multidentate ligands with two to six pyridyl coordination sites. The corresponding complexes of linear porphyrin oligomers were also investigated. The results reveal that the stepwise effective molarities (EMs) for the third through sixth intramolecular coordination events with the cyclic hexamer are extremely high (EM = 10(2)-10(3) M), whereas the values for the linear porphyrin oligomers are modest (EM approximate to 0.05 M). The speciation profiles for the denaturation reactions demonstrate that intermediate species are not significantly populated and that these equilibria are well described by a highly cooperative two-state model.

  DOI：

  10.1021/ja209254r
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 24.0h， 生成 4-[4-(2-phenylethynyl)phenyl]pyridine
  参考文献：
  名称：

  Stepwise Effective Molarities in Porphyrin Oligomer Complexes: Preorganization Results in Exceptionally Strong Chelate Cooperativity

  摘要：

  Complexes of zinc porphyrin oligomers with multivalent ligands can be denatured by adding a large excess of a monodentate ligand, such as quinuclidine. We have used denaturation titrations to determine the stabilities of the complexes of a cyclic zinc-porphyrin hexamer with multidentate ligands with two to six pyridyl coordination sites. The corresponding complexes of linear porphyrin oligomers were also investigated. The results reveal that the stepwise effective molarities (EMs) for the third through sixth intramolecular coordination events with the cyclic hexamer are extremely high (EM = 10(2)-10(3) M), whereas the values for the linear porphyrin oligomers are modest (EM approximate to 0.05 M). The speciation profiles for the denaturation reactions demonstrate that intermediate species are not significantly populated and that these equilibria are well described by a highly cooperative two-state model.

  DOI：

  10.1021/ja209254r

文献信息

• Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand
  作者：Wei Chen、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.2c02796

  日期：2022.9.30

  cross-couplings of nitroarenes and heteroarylboronate esters has been developed. A number of heterobiaryl compounds containing pyridine, pyrimidine, quinoline, furan, thiophene, and pyrazole were prepared using [Pd(cinnamyl)Cl]2/2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the catalysts in good to excellent yields. The synthetic practicality of this approach is demonstrated through

  已经开发了钯催化的硝基芳烃和杂芳基硼酸酯的 Suzuki-Miyaura 交叉偶联。使用[Pd(肉桂基)Cl] 2 /2-芳基-5-(2,4,6-三异丙基苯基)-2,3-制备了许多含有吡啶、嘧啶、喹啉、呋喃、噻吩和吡唑的杂二芳基化合物咪唑亚基[1,5- a ]吡啶作为催化剂，收率良好。这种方法的合成实用性通过类药物分子的合成得到证明。
• Application of hindered ether solvents for palladium catalyzed Suzuki–Miyaura, Sonogashira and cascade Sonogashira cross-coupling reactions
  作者：Suwiwat Sangon、Nontipa Supanchaiyamat、James Sherwood、Duncan J. Macquarrie、Pakin Noppawan、Andrew J. Hunt

  DOI：10.1039/d3ob00118k

  日期：——

  substrates, 71–89% in TMO and 63–92% in DEDMO. In addition, a Sonogashira reaction exhibited the excellent yields of 85–99% performed in TMO, which was significantly higher than traditional volatile organic solvents, THF or toluene, and higher than those reported for another non-peroxide forming ether, namely eucalyptol. Cascade Sonogashira reactions utilizing a simple annulation methodology were particularly

  交叉偶联和级联反应通常依赖于不可持续且有毒的挥发性有机溶剂。2,2,5,5-四甲基氧戊环 (TMO) 和 2,5-二乙基-2,5-二甲基氧戊环 (DEDMO) 本质上都是不形成过氧化物的醚，并且在这项工作中被用作有效、更可持续和用于 Suzuki–Miyaura 和 Sonogashira 反应的潜在生物基替代溶剂。Suzuki–Miyaura 反应在一系列底物上表现出良好的产率，TMO 为 71-89%，DEDMO 为 63-92%。此外，Sonogashira 反应在 TMO 中表现出 85-99% 的优异收率，这明显高于传统的挥发性有机溶剂、THF 或甲苯，也高于报道的另一种非过氧化物形成醚（即桉油精）的收率。使用简单环化方法的级联 Sonogashira 反应在 TMO 中特别有效。此外，一项绿色指标评估证实，使用 TMO 的方法比传统溶剂 THF 和甲苯更可持续、更环保，从而证明了
• US7504505B2
  申请人：——

  公开号：US7504505B2

  公开（公告）日：2009-03-17
• Stepwise Effective Molarities in Porphyrin Oligomer Complexes: Preorganization Results in Exceptionally Strong Chelate Cooperativity
  作者：Hannah J. Hogben、Johannes K. Sprafke、Markus Hoffmann、Miłosz Pawlicki、Harry L. Anderson

  DOI：10.1021/ja209254r

  日期：2011.12.28

  Complexes of zinc porphyrin oligomers with multivalent ligands can be denatured by adding a large excess of a monodentate ligand, such as quinuclidine. We have used denaturation titrations to determine the stabilities of the complexes of a cyclic zinc-porphyrin hexamer with multidentate ligands with two to six pyridyl coordination sites. The corresponding complexes of linear porphyrin oligomers were also investigated. The results reveal that the stepwise effective molarities (EMs) for the third through sixth intramolecular coordination events with the cyclic hexamer are extremely high (EM = 10(2)-10(3) M), whereas the values for the linear porphyrin oligomers are modest (EM approximate to 0.05 M). The speciation profiles for the denaturation reactions demonstrate that intermediate species are not significantly populated and that these equilibria are well described by a highly cooperative two-state model.