3-[(4-ethynylphenyl)ethynyl]pyridine | 1356939-23-5

• 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: 3-[(4-ethynylphenyl)ethynyl]pyridine
• 英文别名: 3-[(4-Ethynylphenyl)ethynyl]pyridine；3-[2-(4-ethynylphenyl)ethynyl]pyridine
• CAS: 1356939-23-5
• 化学式: C₁₅H₉N
• 分子量: 203.243
• InChiKey: XVWRDZYTQVUQLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  1,2-二溴-4,5-二氟苯 、 3-[(4-ethynylphenyl)ethynyl]pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 48.0h， 以51%的产率得到3-[[4-[(2-bromo-4,5-difluorophenyl)ethynyl]phenyl]ethynyl]pyridine
  参考文献：
  名称：

  Extended Self-complementary Halogen Bonded Dimers

  摘要：

  报告了一系列 1,4-二乙炔基苯桥接吡啶基多氟碘基和多氟溴苯基的 X 射线结构，其设计目的是在固态下形成自互补二聚体。化合物 2-[[4-[(3-溴四氟苯基)乙炔基]苯基]乙炔基]吡啶 1 结晶于三linic 空间群 P-1，单胞参数 a = 6.3332(4) (Å), b = 7.4288(4) (Å), c =  17.8897(10) (Å) 和 α = 91.0980(10)°, β = 90.8580(10)° 和 γ = 94.3830(10)°.不对称单元包含一个独特的分子，是自互补的卤键二聚体。化合物 2，3-[[4-[(2-溴四氟苯基)乙炔基]苯基]乙炔基]吡啶和化合物 3，3-[[4-[(2-碘四氟苯基)乙炔基]苯基]乙炔基]吡啶都在三linic 空间群 P-1 中晶体化，且结构相同，单胞参数 a = 6.1324(13) (Å), b = 11.264(2) (Å), c = 13.064(3) (Å), α = 66.646(3)°, β = 89.736(3)°, γ = 87.726(3)° for 2 and a = 6.1671(5) (Å), b = 11.2571(9) (Å), c = 13.3083(11) (Å), α = 66.2870(10)°, β = 88.1990(10)°, γ = 87.3820(10)° 。在这两种结构中，分子基本上以平面自互补卤键二聚体的形式组装。相反，3-[[4-[(2-溴-4,5-二氟苯基)乙炔基]苯基]乙炔基]吡啶 4 结晶于单斜空间群 P21/c，单胞参数 a = 18.7881（7）（埃），b = 3.83820（10）（埃），c = 22.9321（9）（埃），α = γ = 90°，β = 102.6180（10）°，并以 C-H-N 氢键二聚体为特征。报告了一系列 1,4-二乙炔基苯桥接吡啶基多氟碘苯和多氟溴苯形成的自互补卤键二聚体。

  DOI：

  10.1007/s10870-015-0616-9
• 作为产物：
  描述：

  对溴碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 42.0h， 生成 3-[(4-ethynylphenyl)ethynyl]pyridine
  参考文献：
  名称：

  金属碳素超分子Pd6L12聚集体的类似轮烷的笼中环结构基序。

  摘要：

  一个基于BODIPY的双（3-吡啶基）配体在与四价钯（II）阳离子配位后经历自组装，形成具有前所未有的结构基序的Pd 6 L 12金属超分子组装体，类似于轮烷样的笼中环排列。在这种组装中，配体采用两种不同的构象-一个C形构象形成一个Pd 2 L 4笼，该笼位于Pd 4 L 8的中心由W型构象的配体组成的环。这种组装在机械意义上不是机械联锁的，而是仅通过外围BODIPY生色团与配体骨架之间的吸引π堆积以及长烷氧基链之间的吸引范德华相互作用来稳定。结果，两个组件的共同布置导致非常有效的空间填充。整体结构可以说是轮状烷状组件，带有金属超分子笼，形成金属超分子环中的轴。这种独特的结构基序可以通过ESI质谱，NMR光谱和X射线晶体学进行表征。

  DOI：

  10.1002/anie.201806814

文献信息

• Robust R22(8) hydrogen bonded dimer for crystal engineering of glycoluril derivatives
  作者：Jungang Wang、Jiachen Xiang、Anxin Wu、Xianggao Meng

  DOI：10.1039/c3ce41702f

  日期：——

  A series of glycoluril derivatives 1–3 were examined through crystallographic characterization to reveal a highly conserved amide⋯amide homosynthon, with intermolecular R22(8) hydrogen bonding interactions. As expected, the intermolecular hydrogen bonding interactions promoted the dimerization of the building blocks 1–3, even in the presence of competing pyridine rings and various solvent molecules. These robust dimer synthons were then connected to form a one-dimensional chain through C–H⋯O interactions and further extended to a two-dimensional layer by additional C–H⋯π interactions. This robust hydrogen bond motif was achieved without interference from competing intermolecular interactions and significant changes in the hydrocarbon core, and as such has much potential for application as a supramolecular synthon for solid-state design.

  通过晶体学表征研究了一系列甘氨酰脲衍生物 1-3，发现了一种高度保守的酰胺⋯酰胺同源物，其分子间存在 R22(8) 氢键相互作用。正如预期的那样，分子间氢键相互作用促进了结构单元 1-3 的二聚化，即使在存在竞争性吡啶环和各种溶剂分子的情况下也是如此。然后，通过 C-H⋯O 相互作用，这些强健的二聚体合子连接成一维链，并通过额外的 C-H⋯π 相互作用进一步延伸到二维层。这种稳健的氢键图案是在没有竞争性分子间相互作用的干扰和碳氢化合物核心发生重大变化的情况下实现的，因此具有作为固态设计超分子合成物的巨大应用潜力。
• Synthesis, characterization, photoluminescence and optical properties of heterobimetallic Cu/Ru hybrid complexes composed of coordination and organometallic sites
  作者：B.G. Bharate、A.N. Jadhav、S.S. Chavan

  DOI：10.1016/j.poly.2011.11.047

  日期：2012.2

  A new series of heterobimetallic complexes of the type [Cu(L1-3)(NC5H4C CRu(dppe)(2)Cl)l] (3-5) and [Cu(L1-3)(NC5H4C CC6H4C CRu(dppe)(2)Cl)l] (6-8) have been prepared by the reaction of trans-[RuCl (dppe)(2)(C=C-PY-3)] (1) and trans-[RuCl(dppe)(2)(C CC6FLIC C-PY-3)] (2) with copper(I) in the presence of Schiff base ligands L1-3 (where L-1 = N-(2-pyridylmethylene)phenylamine, L-2 = 4-bromo-N-(pyridylmethylene)phenylamine and L-3 = 4-nitro-N-(2-pyridylmethylene)phenylamine). All the complexes were characterized on the basis of elemental analysis, IR, UV-Vis, H-1 NMR, P-31 NMR and mass spectral studies. The electrochemical behavior of the complexes indicates a quasireversible redox behavior corresponding to Cu(I)/Cu(II) and Ru(II)/Ru(III) couples. All the complexes exhibit intra-ligand (pi -> pi*) fluorescence with a high quantum yield in dichloromethane. The second harmonic generation (SHG) efficiency of the complexes was measured by the Kurtz-powder technique, which indicates that all the complexes possess promising potential for the application as useful non-linear optical (NLO) materials. (C) 2011 Elsevier Ltd. All rights reserved.
• Heterobimetallic M(II)/Ru(II) (M=Ni, Zn) complexes containing coordination and organometallic sites: Synthesis, characterization, luminescence and NLO properties
  作者：S.S. Chavan、B.G. Bharate

  DOI：10.1016/j.ica.2012.09.018

  日期：2013.1

  Some heterobimetallic complexes of the type [Ni(L1-3)(NC5H4C CC6H4C CRu(dppe)(2)Cl)] (1a-c) and [Zn(L1-3)(NC5H4C CC6H4C CRu(dppe)(2)Cl)] (2a-c) have been prepared by the reaction of trans-[RuCl(dppe)(2)(C CC6H4C C-py-3)] (1) with Ni(II) and Zn(II) in presence of Schiff base ligands L1-3 (where L-1 = 2-(pyrrole-2-yl-methylidine)aminophenol, L-2 = 5-bromo-2-(pyrrole-2-yl-methylidine)aminophenol and L-3 = 5-nitro-2-(pyrrole-2-yl-methylidine) aminophenol. All the complexes were characterized on the basis of elemental analyses, IR, UV-Vis, H-1 NMR, and P-31 NMR spectral studies and compound trans-[RuCl(dppe)(2)(C CC6H4C C-py-3)] (1) by single crystal X-ray analysis. Quasireversible redox behavior is accounted for all complexes corresponding to Ni(II)/Ni(III) and Ru(II)/Ru(III) for 1a-c and Ru(II)/Ru(III) for 2a-c. All complexes exhibit intra-ligand (pi -> pi*) fluorescence with high quantum yield in dimethylformamide. The second harmonic generation (SHG) efficiency of the complexes was measured by Kurtz-powder technique indicating that all complexes display the second harmonic generation (SHG) property. (C) 2012 Elsevier B. V. All rights reserved.
• A Rotaxane-like Cage-in-Ring Structural Motif for a Metallosupramolecular Pd₆ L₁₂ Aggregate
  作者：Matthias Käseborn、Julian J. Holstein、Guido H. Clever、Arne Lützen

  DOI：10.1002/anie.201806814

  日期：2018.9.10

  bis(3‐pyridyl) ligand undergoes self‐assembly upon coordination to tetravalent palladium(II) cations to form a Pd6L12 metallosupramolecular assembly with an unprecedented structural motif that resembles a rotaxane‐like cage‐in‐ring arrangement. In this assembly the ligand adopts two different conformations—a C‐shaped one to form a Pd2L4 cage which is located in the center of a Pd4L8 ring consisting of ligands

  一个基于BODIPY的双（3-吡啶基）配体在与四价钯（II）阳离子配位后经历自组装，形成具有前所未有的结构基序的Pd 6 L 12金属超分子组装体，类似于轮烷样的笼中环排列。在这种组装中，配体采用两种不同的构象-一个C形构象形成一个Pd 2 L 4笼，该笼位于Pd 4 L 8的中心由W型构象的配体组成的环。这种组装在机械意义上不是机械联锁的，而是仅通过外围BODIPY生色团与配体骨架之间的吸引π堆积以及长烷氧基链之间的吸引范德华相互作用来稳定。结果，两个组件的共同布置导致非常有效的空间填充。整体结构可以说是轮状烷状组件，带有金属超分子笼，形成金属超分子环中的轴。这种独特的结构基序可以通过ESI质谱，NMR光谱和X射线晶体学进行表征。
• Extended Self-complementary Halogen Bonded Dimers
  作者：Lisa M. Kirchner、Nathan P. Bowling、Eric Bosch

  DOI：10.1007/s10870-015-0616-9

  日期：2015.12

  The X-ray structure of a series of 1,4-diethynylbenzene bridged pyridyl polyfluoroiodo- and polyfluorobromophenyls designed to form self-complementary dimers in the solid state are reported. The compound 2-[[4-[(3-bromotetrafluorophenyl)ethynyl]phenyl]ethynyl]pyridine, 1, crystalized in the triclinic space group P-1 with unit cell parameters a = 6.3332(4) (Å), b = 7.4288(4) (Å), c =  17.8897(10) (Å) and α = 91.0980(10)°, β = 90.8580(10)° and γ = 94.3830(10)°. The asymmetric unit contains a unique molecule as a self-complementary halogen bonded dimer. Compounds 2, 3-[[4-[(2-bromotetrafluorophenyl)ethynyl]phenyl]ethynyl]pyridine and 3, 3-[[4-[(2-iodotetrafluorophenyl)ethynyl]phenyl]ethynyl]pyridine both crystalized in the triclinic space group P-1 and are isostructural with unit cell parameters a = 6.1324(13) (Å), b = 11.264(2) (Å), c = 13.064(3) (Å), α = 66.646(3)°, β = 89.736(3)°, γ = 87.726(3)° for 2 and a = 6.1671(5) (Å), b = 11. 2571(9) (Å), c = 13.3083(11) (Å), α = 66.2870(10)°, β = 88.1990(10)°, γ = 87.3820(10)° for 3. In both structures the molecules assemble as essentially planar self-complementary halogen bonded dimers. In contrast 3-[[4-[(2-bromo-4,5-difluorophenyl)ethynyl]phenyl]ethynyl]pyridine, 4, crystalized in the monoclinic space group P21/c with unit cell parameters a = 18.7881(7) (Å), b = 3.83820(10) (Å), c = 22.9321(9) (Å), α = γ = 90°, β = 102.6180(10)° and featured a C–H···N hydrogen bonded dimer. The formation of self-complementary halogen bonded dimers with a series of 1,4-diethynylbenzene bridged pyridyl polyfluoroiodo- and polyfluorobromophenyls is reported.

  报告了一系列 1,4-二乙炔基苯桥接吡啶基多氟碘基和多氟溴苯基的 X 射线结构，其设计目的是在固态下形成自互补二聚体。化合物 2-[[4-[(3-溴四氟苯基)乙炔基]苯基]乙炔基]吡啶 1 结晶于三linic 空间群 P-1，单胞参数 a = 6.3332(4) (Å), b = 7.4288(4) (Å), c =  17.8897(10) (Å) 和 α = 91.0980(10)°, β = 90.8580(10)° 和 γ = 94.3830(10)°.不对称单元包含一个独特的分子，是自互补的卤键二聚体。化合物 2，3-[[4-[(2-溴四氟苯基)乙炔基]苯基]乙炔基]吡啶和化合物 3，3-[[4-[(2-碘四氟苯基)乙炔基]苯基]乙炔基]吡啶都在三linic 空间群 P-1 中晶体化，且结构相同，单胞参数 a = 6.1324(13) (Å), b = 11.264(2) (Å), c = 13.064(3) (Å), α = 66.646(3)°, β = 89.736(3)°, γ = 87.726(3)° for 2 and a = 6.1671(5) (Å), b = 11.2571(9) (Å), c = 13.3083(11) (Å), α = 66.2870(10)°, β = 88.1990(10)°, γ = 87.3820(10)° 。在这两种结构中，分子基本上以平面自互补卤键二聚体的形式组装。相反，3-[[4-[(2-溴-4,5-二氟苯基)乙炔基]苯基]乙炔基]吡啶 4 结晶于单斜空间群 P21/c，单胞参数 a = 18.7881（7）（埃），b = 3.83820（10）（埃），c = 22.9321（9）（埃），α = γ = 90°，β = 102.6180（10）°，并以 C-H-N 氢键二聚体为特征。报告了一系列 1,4-二乙炔基苯桥接吡啶基多氟碘苯和多氟溴苯形成的自互补卤键二聚体。