4-((4-乙炔苯基)乙炔)苯甲酸 | 866825-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-((4-乙炔苯基)乙炔)苯甲酸
• 英文名称: 4-((4-ethynylphenyl)ethynyl)benzoic acid
• 英文别名: 4-((4-Ethynylphenyl)ethynyl)benzoic acid；4-[2-(4-ethynylphenyl)ethynyl]benzoic acid
• CAS: 866825-55-0
• 化学式: C₁₇H₁₀O₂
• 分子量: 246.265
• InChiKey: IGDGMIRIOMACJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((4-乙炔苯基)乙炔)苯甲酸 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 caesium carbonate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.67h， 生成 methyl 16-{4-[2-(4-{2-[4-({[2-(hydroxymethyl)-4-(methylethylidene)-5-oxo-2-2,3-dihydrofuryl]methyl}oxycarbonyl)phenyl]ethynyl}phenyl)ethynyl]phenoxy}hexadecanoate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 27. Modulation of Membrane Translocation of Protein Kinase C (PKC) Isozymes α and δ by Diacylglycerol Lactones (DAG-lactones) Containing Rigid-Rod Acyl Groups

  摘要：

  Highly rigid and geometrically well-defined rods composed of ethynylene-substituted aromatic spacers [oligo(p-phenyleneethynylene), OPE] were incorporated as acyl moieties on diacylglycerol lactones (DAG-lactones) and investigated for their ability to bind to protein kinase C (PKC) and translocate PKC alpha and delta isoforms to plasma and internal membranes. The kinetics of PKC translocation were correlated with biological responses, viz. ERK phosphorylation, induction of IL-6 secretion, inhibition of cell proliferation, and induction of cellular attachment, that display very different time courses. Because OPE rods assemble through noncovalent forces and form stable films, they may influence the microdomain environment around the DAG-lactone membrane-binding site. A comparison of two DAG-lactones (1 and 10), one with two PE units (1) and the other with an equivalent flexible acyl chain (10) of matching lipophilicity, clearly demonstrated the effect of the rigid OPE chain in substantially prolonging the translocated state of both PKC alpha and delta.

  DOI：

  10.1021/jm061289j
• 作为产物：
  描述：

  (4-溴苯基)乙炔 在 吡啶 、 三乙胺 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 98.0h， 生成 4-((4-乙炔苯基)乙炔)苯甲酸
  参考文献：
  名称：

  通过苯-乙炔使自由电子密度离域：时间分辨红外光谱研究的结构变化1

  摘要：

  我们研究了 1,4-双(2-[4-叔丁基过氧羰基苯基]乙炔基)苯 (1) 和叔丁基 4-(2-{4-[2-(4-苯氧羰基苯基)-1-乙炔基]苯基}-1-乙炔基)过氧苯甲酸酯(2)。355 nm 激光脉冲对 1 和 2 的激发导致芳酰氧基自由基的快速形成。与亚苯基-乙炔基核共轭的未成对电子在发色团的π-系统上基本上离域。这些自由基的 -CC- 振动频率相对于 1 和 2 发生红移，如通过时间分辨红外光谱测量。这种转变归因于自由电子离域导致三键特性的变化。

  DOI：

  10.1021/ja053120l

文献信息

• Evidence for the assembly of carboxyphenylethynyl zinc porphyrins on nanocrystalline TiO2 surfaces
  作者：Chen-Fu Lo、Liyang Luo、Eric Wei-Guang Diau、I-Jy Chang、Ching-Yao Lin

  DOI：10.1039/b516782e

  日期：——

  UV-visible absorption and AFM studies suggest that carboxyphenylethynyl zinc porphyrins aggregate on nanocrystalline TiO2 surfaces in an H-type fashion.

  紫外可见吸收和原子力显微镜研究表明，羧基苯基乙炔基锌卟啉以H型方式聚集在纳米TiO2表面上。
• Merging Supramolecular and Covalent Helical Polymers: Four Helices Within a Single Scaffold
  作者：Zulema Fernández、Berta Fernández、Emilio Quiñoá、Félix Freire

  DOI：10.1021/jacs.1c10327

  日期：2021.12.15

  goal, the poly(acetylene) must adopt a dihedral angle between conjugated double bonds (ω1) higher than 165°. In such cases, the tilting degree (Θ) between the OPE units used as pendant groups is close to 11°, like that observed in supramolecular helical arrays of these molecules. Polymerization of oligo[(p-phenyleneethynylene)n]phenylacetylene monomers (n = 1, 2) bearing L-decyl alaninate as the pendant

  超分子和共价聚合物具有多种结构效应，例如手性放大、螺旋反转、军士和士兵或多数规则等。这些特征与两种材料中的轴向螺旋结构有关，这决定了它们的性能。本文提出了一种结合了螺旋聚合物、超分子（低聚（对亚苯基乙炔基）（OPE））和共价（聚（乙炔）（PA））两个领域的信息和特性的新型材料。为了实现这一目标，聚乙炔必须采用高于 165° 的共轭双键之间的二面角 (ω1)。在这种情况下，用作侧基的 OPE 单元之间的倾斜度 (θ) 接近 11°，就像在这些分子的超分子螺旋阵列中观察到的那样。带有L-癸基丙氨酸酯作为侧基的低聚[(对亚苯基乙炔基) n ]苯乙炔单体( n = 1, 2)的聚合产生了所需的支架。这些聚合物采用拉伸且几乎平面的多烯螺旋，其中 OPE 单元的排列描述了螺旋结构。结果，制备了一种新型多螺旋材料，其ECD光谱以OPE轴向阵列为主。
• Conformationally Constrained Analogues of Diacylglycerol (DAG). 27. Modulation of Membrane Translocation of Protein Kinase C (PKC) Isozymes α and δ by Diacylglycerol Lactones (DAG-<scp>l</scp>actones) Containing Rigid-Rod Acyl Groups
  作者：Krishnan Malolanarasimhan、Noemi Kedei、Dina M. Sigano、James A. Kelley、Christopher C. Lai、Nancy E. Lewin、Robert J. Surawski、Vladimir A. Pavlyukovets、Susan H. Garfield、Stephen Wincovitch、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm061289j

  日期：2007.3.1

  Highly rigid and geometrically well-defined rods composed of ethynylene-substituted aromatic spacers [oligo(p-phenyleneethynylene), OPE] were incorporated as acyl moieties on diacylglycerol lactones (DAG-lactones) and investigated for their ability to bind to protein kinase C (PKC) and translocate PKC alpha and delta isoforms to plasma and internal membranes. The kinetics of PKC translocation were correlated with biological responses, viz. ERK phosphorylation, induction of IL-6 secretion, inhibition of cell proliferation, and induction of cellular attachment, that display very different time courses. Because OPE rods assemble through noncovalent forces and form stable films, they may influence the microdomain environment around the DAG-lactone membrane-binding site. A comparison of two DAG-lactones (1 and 10), one with two PE units (1) and the other with an equivalent flexible acyl chain (10) of matching lipophilicity, clearly demonstrated the effect of the rigid OPE chain in substantially prolonging the translocated state of both PKC alpha and delta.
• Delocalization of Free Electron Density through Phenylene−Ethynylene:  Structural Changes Studied by Time-Resolved Infrared Spectroscopy
  作者：Dmitry E. Polyansky、Evgeny O. Danilov、Sergey V. Voskresensky、Michael A. J. Rodgers、Douglas C. Neckers

  DOI：10.1021/ja053120l

  日期：2005.10.1

  We have studied the photochemistry of 1,4-bis(2-[4-tert-butylperoxycarbonylphenyl]ethynyl)benzene (1) and tert-butyl 4-(2-4-[2-(4-phenyloxycarbonylphenyl)-1-ethynyl]phenyl}-1-ethynyl)peroxybenzoate (2). Excitation of 1 and 2 by a 355-nm laser pulse leads to the rapid formation of aroyloxyl radicals. An unpaired electron conjugated with the phenylene-ethynylene core is substantially delocalized over

  我们研究了 1,4-双(2-[4-叔丁基过氧羰基苯基]乙炔基)苯 (1) 和叔丁基 4-(2-4-[2-(4-苯氧羰基苯基)-1-乙炔基]苯基}-1-乙炔基)过氧苯甲酸酯(2)。355 nm 激光脉冲对 1 和 2 的激发导致芳酰氧基自由基的快速形成。与亚苯基-乙炔基核共轭的未成对电子在发色团的π-系统上基本上离域。这些自由基的 -CC- 振动频率相对于 1 和 2 发生红移，如通过时间分辨红外光谱测量。这种转变归因于自由电子离域导致三键特性的变化。