2-(4'-benzyloxy-3'-chlorobiphenyl-2-yl)benzoxazole | 1239313-08-6

• 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'-benzyloxy-3'-chlorobiphenyl-2-yl)benzoxazole
• 英文别名: 2-[2-(3-Chloro-4-phenylmethoxyphenyl)phenyl]-1,3-benzoxazole；2-[2-(3-chloro-4-phenylmethoxyphenyl)phenyl]-1,3-benzoxazole
• CAS: 1239313-08-6
• 化学式: C₂₆H₁₈ClNO₂
• 分子量: 411.887
• InChiKey: HJDJQJHRTMOECV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-benzyloxy-3'-chlorobiphenyl-2-yl)benzoxazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 30.0~40.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 以80%的产率得到2'-benzoxazol-2-yl-3-chlorobiphenyl-4-ol
  参考文献：
  名称：

  2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation

  摘要：

  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.

  DOI：

  10.1021/ml400500e
• 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 6.0h， 生成 2-(4'-benzyloxy-3'-chlorobiphenyl-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

• 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。
• Cooperative Catalysis by Palladium–Nickel Binary Nanocluster for Suzuki–Miyaura Reaction of <i>Ortho</i>-Heterocycle-Tethered Sterically Hindered Aryl Bromides
  作者：Kapileswar Seth、Priyank Purohit、Asit K. Chakraborti

  DOI：10.1021/ol500587m

  日期：2014.5.2

  The palladium–nickel binary nanocluster is reported as a new catalyst system for Suzuki–Miyaura cross-coupling of ortho-heterocycle-tethered sterically hindered aryl bromides. The inferior results obtained with the reported Pd/Ni salts/complexes or individual Pd/Ni nanoparticles as catalyst reveal the cooperative catalytic effect of the Pd and Ni nanoparticles in the Pd–Ni nanocluster. The broad substrate

  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。
• 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.