2-(4'-methoxybiphenyl-2-yl)benzoxazole | 1239313-01-9

• 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: 2-(4'-methoxybiphenyl-2-yl)benzoxazole
• 英文别名: 2-(4'-methoxy-[1,1'-biphenyl]-2-yl)benzo[d]oxazole；2-[2-(4-Methoxyphenyl)phenyl]-1,3-benzoxazole；2-[2-(4-methoxyphenyl)phenyl]-1,3-benzoxazole
• CAS: 1239313-01-9
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: RPNWWLKDYPWPDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴苯甲酰氯 在 甲烷磺酸 、 nickel(II) chloride hexahydrate 、 四丁基氟化铵 、 potassium carbonate 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.66h， 生成 2-(4'-methoxybiphenyl-2-yl)benzoxazole
  参考文献：
  名称：

  钯-镍二元纳米团簇协同催化邻杂环杂环芳基溴化物的Suzuki-Miyaura反应

  摘要：

  据报道，钯-镍二元纳米团簇是邻杂环固定的位阻芳基溴化物的Suzuki-Miyaura交叉偶联的新催化剂体系。使用已报道的Pd / Ni盐/络合物或单个Pd / Ni纳米粒子作为催化剂所获得的较差结果表明，Pd-Ni纳米簇中Pd和Ni纳米粒子具有协同催化作用。关于2-芳基苯并恶唑部分和硼酸的变化的广泛的底物范围提供了多样性产生和催化剂可再循环性的手段，这标志着明显的优势。

  DOI：

  10.1021/ol500587m

文献信息

• Catalytic constructive deoxygenation of lignin-derived phenols: new C–C bond formation processes from imidazole-sulfonates and ether cleavage reactions
  作者：Stuart M. Leckie、Gavin J. Harkness、Matthew L. Clarke

  DOI：10.1039/c4cc04939j

  日期：——

  feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

  作为旨在利用木质素作为含氧量较小的精细化学品的化学原料的计划的一部分，展示了几种利用愈创木酚咪唑磺酸盐的催化CC键形成反应。这些包括格利雅（Grignard），无毒氰化物源，苯并恶唑和硝基甲烷的交叉偶联。改良的Meyers反应用于在苯并恶唑官能化的茴香醚上进行第二次结构性脱氧。
• C–O Bond Activation by Nickel–Palladium Hetero-Bimetallic Nanoparticles for Suzuki–Miyaura Reaction of Bioactive Heterocycle-Tethered Sterically Hindered Aryl Carbonates
  作者：Priyank Purohit、Kapileswar Seth、Asim Kumar、Asit K. Chakraborti

  DOI：10.1021/acscatal.6b02912

  日期：2017.4.7

  Ni–Pd binary nanoclusters are reported for the activation of the C–O bond for Suzuki–Miyaura cross-coupling of bioactive heterocycle-tethered sterically hindered aryl carbonates with aryl boronic acids. The reaction does not take place in the presence of either the Pd or Ni salts/complexes or the individual Pd or Ni nanoparticles, indicating ensembling cooperativity between the Pd and Ni nanoparticles

  据报道，Ni-Pd二元纳米团簇可激活Suzuki-Miyaura将具有生物活性的杂环束缚的空间受阻芳基碳酸酯与芳基硼酸的C-O键活化。该反应不会在Pd或Ni盐/络合物或单个Pd或Ni纳米粒子的存在下发生，这表明Pd和Ni纳米粒子在激活C-O键上具有协同作用。
• Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds
  作者：Kapileswar Seth、Mohit Maingle、Steeva Sunny、Loddipalle Sheeba、Firojkhan Rajekhan Pathan

  DOI：10.1055/a-2193-4804

  日期：2024.1

  were used as innate directing groups for Pd(II)- and Ru(II)-catalyzed C–H arylation of the biorelevant heterocycles 2-arylbenzoxazole and 2-arylbenzothiazole with diverse iodoarenes; palladium and ruthenium catalysis could be used complementarily. The use of σ-donor ligands, such as N,N-dimethylacetamide in the Pd(II) catalytic cycle, and σ-donor/π-acceptor ligands, such as PPh3 in the Ru(II) catalytic

  苯并恶唑和苯并噻唑部分用作 Pd(II) 和 Ru(II) 催化的生物相关杂环 2-芳基苯并恶唑和 2-芳基苯并噻唑与多种碘芳烃的 C-H 芳基化的固有导向基团；钯和钌催化可以互补使用。使用σ-供体配体（例如Pd（II）催化循环中的N，N-二甲基乙酰胺）和σ-供体/π-受体配体（例如Ru（II）催化循环中的PPh 3 ）增强了芳基化速率显着，并且受2-芳基苯并恶唑或2-芳基苯并噻唑的C2-芳基环的C-H酸度控制。这些方法对于偶联配偶体而言具有广泛的底物范围，以适应电子中性、富电子以及缺电子的碘芳烃；2-芳基苯并恶唑或2-芳基苯并噻唑的C2-芳基单元在邻位C -H位置表现出高度的位点选择性，仅以良好的产率提供单芳基化衍生物；该反应具有官能团耐受性，适用于克级生产。
• 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation
  作者：Kapileswar Seth、Sanjeev K. Garg、Raj Kumar、Priyank Purohit、Vachan S. Meena、Rohit Goyal、Uttam C. Banerjee、Asit K. Chakraborti

  DOI：10.1021/ml400500e

  日期：2014.5.8

  The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2). The 2-(2-arylphenyl)benzoxazoles 3a-m have been synthesized by Suzuki reaction of 2-(2-bromophenyl)benzoxazole. Further synthetic manipulation of 3f and 3i led to 3o and 3n, respectively. The compounds 3g, 3n, and 3o selectively inhibited COX-2 with selectivity index of 3n much better than that of the COX-2 selective NSAID celecoxib. The in vivo anti-inflammatory potency of 3g and 3n is comparable to that of celecoxib and the nonselective NSAID diclofenac at two different doses, and 30 showed better potency compared to these clinically used NSAIDs.