4-((4-butylphenyl)ethynyl)-1,1'-biphenyl | 655251-27-7

• 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: 4-((4-butylphenyl)ethynyl)-1,1'-biphenyl
• 英文别名: 4-(4-butyl-phenylethynyl)-biphenyl；1-Butyl-4-[2-(4-phenylphenyl)ethynyl]benzene
• CAS: 655251-27-7
• 化学式: C₂₄H₂₂
• 分子量: 310.439
• InChiKey: LPYBTHMGSWAPJM-UHFFFAOYSA-N

物化性质

• 沸点：
  459.4±34.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-((4-butylphenyl)ethynyl)-1,1'-biphenyl 在 高碘酸 作用下， 以 neat (no solvent) 为溶剂， 以82%的产率得到1-([1,1'-biphenyl]-4-yl)-2-(4-butylphenyl)ethane-1,2-dione
  参考文献：
  名称：

  通过机械化学模拟臭氧分解：使用 H5IO6 将内部炔烃转化为 1,2-二酮

  摘要：

  高碘酸是唯一的氧化剂，可通过机械化学作用从多种炔烃中生成 1,2-二酮，有效模拟臭氧的反应性。它环保、性价比高，并且表现出对不同群体的包容性。

  DOI：

  10.1002/chem.202401027
• 作为产物：
  描述：

  4-溴代联苯 、 4-丁基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.25h， 以64%的产率得到4-((4-butylphenyl)ethynyl)-1,1'-biphenyl
  参考文献：
  名称：

  联苯和芴基邻甲硼烷基化合物：联苯环畸变引起的光物理性质改变

  摘要：

  Four biphenyl- and fluorene-based o-carboranyl compounds, 4-[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-biphenyl (1B), 4,4 ''-bis[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-biphenyl (2B), 2-[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-fluorene (1F), and 2,7-bis[2-(p-n-butylphenyl)-1-o-carboran-1-yl]fluorene (2F), were prepared and fully characterized by multinuclear NMR spectroscopy and elemental analysis. The crystal structures of 1B and 2B, analyzed by single-crystal X-ray diffraction, exhibited distinct distortions of the central biphenyl rings with dihedral angles of 44.2 and 33.1 degrees. In photoluminescence measurements, fluorene-based carboranyl compounds in the rigid state (e.g., in solution at 77 K and as films) exhibited a noticeable emission in the low-energy region below 400 nm. 1F displayed a low-energy emissive trace in solution at ambient temperature, whereas biphenyl-based carboranes mainly exhibited high-energy emissions above 400 nm. TD-DFT calculations on the first excited singlet (S-1) state of each compound suggested that the emission in the low-energy region involves intramolecular charge transfer (ICT) between the carborane and central phenylene rings, indicating that the radiative decay of these ICT bands could be enhanced by preventing the distortion of the central biphenyl groups. Furthermore, less distortion on the biphenyl rings of the biphenyl-based analogues at Si in the optimized structures supports that these phenylenes must be flat for the formation of stable excited states. Comparison of the quantum efficiency (Phi(PL)) and radiative decay constants (k(r)) of the o-carboranes also reveals definitively that the structural features of the biphenyl groups can have a decisive effect on those photophysical properties.

  DOI：

  10.1021/acs.organomet.7b00093

文献信息

• Naphthoquinone-Directed C–H Annulation and C_sp³–H Bond Cleavage: One-Pot Synthesis of Tetracyclic Naphthoxazoles
  作者：Meining Wang、Chi Zhang、Li-Ping Sun、Chunyong Ding、Ao Zhang

  DOI：10.1021/jo500572u

  日期：2014.5.16

  One-pot synthesis of tetracyclic naphthoxazole derivatives from electron-deficient naphthoquinones and alkynes was achieved via Rh(III)-catalyzed C–H activation and Csp3–H bond cleavage for the first time. This approach proceeds through a tandem cascade process involving substrate tautomerization, C–H activation, oxidative addition, cyclization, and aromatization. In addition, broad substrate scope

  首次通过Rh（III）催化的C–H活化和C sp 3 –H键裂解，从缺电子的萘醌和炔烃一锅合成四环萘恶唑衍生物。这种方法通过串联级联过程进行，涉及底物互变异构，CH活化，氧化加成，环化和芳构化。另外，广泛的底物范围，简单的起始原料和空间耐受性使得该策略具有很大的实用性。
• Polymerisation Initiator
  申请人：Merck Patent GmbH

  公开号：EP1388538B1

  公开（公告）日：2010-09-01
• Biphenyl- and Fluorene-Based <i>o</i>-Carboranyl Compounds: Alteration of Photophysical Properties by Distortion of Biphenyl Rings
  作者：Nara Shin、Seokhyeon Yu、Ji Hye Lee、Hyonseok Hwang、Kang Mun Lee

  DOI：10.1021/acs.organomet.7b00093

  日期：2017.4.24

  Four biphenyl- and fluorene-based o-carboranyl compounds, 4-[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-biphenyl (1B), 4,4 ''-bis[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-biphenyl (2B), 2-[2-(p-n-butylphenyl)-1-o-carboran-1-yl]-fluorene (1F), and 2,7-bis[2-(p-n-butylphenyl)-1-o-carboran-1-yl]fluorene (2F), were prepared and fully characterized by multinuclear NMR spectroscopy and elemental analysis. The crystal structures of 1B and 2B, analyzed by single-crystal X-ray diffraction, exhibited distinct distortions of the central biphenyl rings with dihedral angles of 44.2 and 33.1 degrees. In photoluminescence measurements, fluorene-based carboranyl compounds in the rigid state (e.g., in solution at 77 K and as films) exhibited a noticeable emission in the low-energy region below 400 nm. 1F displayed a low-energy emissive trace in solution at ambient temperature, whereas biphenyl-based carboranes mainly exhibited high-energy emissions above 400 nm. TD-DFT calculations on the first excited singlet (S-1) state of each compound suggested that the emission in the low-energy region involves intramolecular charge transfer (ICT) between the carborane and central phenylene rings, indicating that the radiative decay of these ICT bands could be enhanced by preventing the distortion of the central biphenyl groups. Furthermore, less distortion on the biphenyl rings of the biphenyl-based analogues at Si in the optimized structures supports that these phenylenes must be flat for the formation of stable excited states. Comparison of the quantum efficiency (Phi(PL)) and radiative decay constants (k(r)) of the o-carboranes also reveals definitively that the structural features of the biphenyl groups can have a decisive effect on those photophysical properties.
• Mimicking Ozonolysis via Mechanochemistry: Internal Alkynes to 1,2‐Diketones using H5IO6
  作者：Pravat Nayek、Prasenjit Mal

  DOI：10.1002/chem.202401027

  日期：——

  Periodic acid is the sole oxidizing agent, yielding 1,2-diketones mechanochemically from diverse alkynes, effectively emulating ozone‘s reactivity. It is environmentally friendly, cost-effective, and shows tolerance of different groups.

  高碘酸是唯一的氧化剂，可通过机械化学作用从多种炔烃中生成 1,2-二酮，有效模拟臭氧的反应性。它环保、性价比高，并且表现出对不同群体的包容性。