4-(4-chlorobenzyl)-1,1'-biphenyl | 30203-86-2

• 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-chlorobenzyl)-1,1'-biphenyl
• 英文别名: p-Chlor-p'-phenyldiphenylmethan；4-[(4-chlorophenyl)methyl]biphenyl；1-Chloro-4-[(4-phenylphenyl)methyl]benzene
• CAS: 30203-86-2
• 化学式: C₁₉H₁₅Cl
• 分子量: 278.781
• InChiKey: AJDFCPUQWYYCGG-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C(Solvent: Acetic acid)
• 沸点：
  410.1±24.0 °C(predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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-chlorobenzyl)-1,1'-biphenyl 在 正丁基锂 、 sodium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 1.0h， 生成 VUF 5864
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of the First Nonpeptidergic Inverse Agonists for the Human Cytomegalovirus Encoded Chemokine Receptor US28

  摘要：

  US28 is a human cytomegalovirus (HCMV) encoded G-protein-coupled receptor that signals in a constitutively active manner. Recently, we identified 1 {5-(4-(4-chlorophenyl)-4-hydroxy-piperidin-1-yl)-2,2-diphenylpentanenitrile} as the first reported nonpeptidergic inverse agonist for a viral-encoded chemokine receptor. Interestingly, this compound is able to partially inhibit the viral entry of HIV-1. In this study we describe the synthesis of 1 and several of its analogues and unique structure-activity relationships for this first class of small-molecule ligands for the chemokine receptor US28. Moreover, the compounds have been pharmacologically characterized as inverse agonists on US28. By modification of lead structure 1, it is shown that a 4-phenylpiperidine moiety is essential for affinity and activity. Other structural features of 1 are shown to be of less importance. These compounds define the first SAR of ligands on a viral GPCR (US28) and may therefore serve as important tools to investigate the significance of US28-mediated constitutive activity during viral infection.

  DOI：

  10.1021/jm050418d
• 作为产物：
  描述：

  4'-phenyl-4-chloro benzophenone 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 4-(4-chlorobenzyl)-1,1'-biphenyl
  参考文献：
  名称：

  苯中卤素取代的二苯基甲烷的光化学苯基化和氧化

  摘要：

  数种氯和溴代二苯甲烷在氮气氛下在苯中光解为相应的苯基化和还原的化合物。在空气存在下的光解还产生了酮类产物，其形成是通过卤素催化的光氧化反应来解释的。

  DOI：

  10.1039/j39700002586

文献信息

• Photochemical phenylation and oxidation of halogen-substituted di-phenylmethanes in benzene
  作者：G. E. Robinson、J. M. Vernon

  DOI：10.1039/j39700002586

  日期：——

  Several chloro- and bromo-diphenylmethanes are photolysed in benzene under nitrogen to the corresponding phenylated and reduced compounds. Photolysis in presence of air gives additionally ketonic products, whose formation is explained in terms of a halogen-catalysed photo-oxidation reaction.

  数种氯和溴代二苯甲烷在氮气氛下在苯中光解为相应的苯基化和还原的化合物。在空气存在下的光解还产生了酮类产物，其形成是通过卤素催化的光氧化反应来解释的。
• 10.1002/anie.202405902
  作者：Lukas, Florian、Findlay, Michael T.、Fillols, Méritxell、Templ, Johanna、Savino, Elia、Martin, Benjamin、Allmendinger, Simon、Furegati, Markus、Noël, Timothy

  DOI：10.1002/anie.202405902

  日期：——

  Decarboxylative C(sp2)−C(sp3) bond formation using a metallaphotoredox approach is a key method for rapidly building molecular complexity. In this work, we demonstrate that graphitic carbon nitride, a heterogeneous semiconductor, can act as a suitable photocatalyst to induce decarboxylative bond formation. A broad scope of coupling partners is presented, in addition to photocatalyst recycling, analysis,

  使用金属光氧化还原方法形成脱羧 C(sp 2 )−C(sp 3 ) 键是快速构建分子复杂性的关键方法。在这项工作中，我们证明了石墨氮化碳（一种异质半导体）可以作为合适的光催化剂来诱导脱羧键的形成。除了光催化剂回收、分析和机理研究之外，还介绍了广泛的耦合伙伴。
• Manih, Rudolf M.; Myrboh, Bekington, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 1, p. 146 - 151
  作者：Manih, Rudolf M.、Myrboh, Bekington

  DOI：——

  日期：——
• Synthesis and Structure−Activity Relationship of the First Nonpeptidergic Inverse Agonists for the Human Cytomegalovirus Encoded Chemokine Receptor US28
  作者：Janneke W. Hulshof、Paola Casarosa、Wiro M. P. B. Menge、Leena M. S. Kuusisto、Henk van der Goot、Martine J. Smit、Iwan J. P. de Esch、Rob Leurs

  DOI：10.1021/jm050418d

  日期：2005.10.1

  US28 is a human cytomegalovirus (HCMV) encoded G-protein-coupled receptor that signals in a constitutively active manner. Recently, we identified 1 5-(4-(4-chlorophenyl)-4-hydroxy-piperidin-1-yl)-2,2-diphenylpentanenitrile} as the first reported nonpeptidergic inverse agonist for a viral-encoded chemokine receptor. Interestingly, this compound is able to partially inhibit the viral entry of HIV-1. In this study we describe the synthesis of 1 and several of its analogues and unique structure-activity relationships for this first class of small-molecule ligands for the chemokine receptor US28. Moreover, the compounds have been pharmacologically characterized as inverse agonists on US28. By modification of lead structure 1, it is shown that a 4-phenylpiperidine moiety is essential for affinity and activity. Other structural features of 1 are shown to be of less importance. These compounds define the first SAR of ligands on a viral GPCR (US28) and may therefore serve as important tools to investigate the significance of US28-mediated constitutive activity during viral infection.