1-Azido-3-phenoxybenzene | 1197231-91-6

• 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: 1-Azido-3-phenoxybenzene
• CAS: 1197231-91-6
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: NXGMHNKTXXPWMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Azido-3-phenoxybenzene 在 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (2-aminophenyl)(1-(3-phenoxyphenyl)-1H-1,2,3-triazol-4-yl)methanone
  参考文献：
  名称：

  1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α

  摘要：

  Estrogen-related receptor a is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2,3-triazoles as novel suppressors of ERR alpha transcriptional functions. The most promising compound, 2-aminophenyl-(1-(3-isopropylpheny1)-1H-1,2,3-triazol-4-yl)methanone (14n), potently suppressed the transcriptional functions of ERR alpha with IC50 = 0.021 mu M in a cell-based reporter gene assay and also decreased both the mRNA levels and the protein levels of ERR alpha and the downstream targets. This compound inhibited the proliferation and migration of breast cancer cells with high level of ERR alpha. Preliminary pharmacolcinetic studies suggested that it possessed a good pharmacokinetic profile with an oral bioavailability of 71.8%. The compounds may serve as novel small molecule probes for further validation of ERR alpha as a molecular target for anticancer drug development.

  DOI：

  10.1021/jm4003928
• 作为产物：
  描述：

  3-苯氧基苯胺 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 1-Azido-3-phenoxybenzene
  参考文献：
  名称：

  1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α

  摘要：

  Estrogen-related receptor a is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2,3-triazoles as novel suppressors of ERR alpha transcriptional functions. The most promising compound, 2-aminophenyl-(1-(3-isopropylpheny1)-1H-1,2,3-triazol-4-yl)methanone (14n), potently suppressed the transcriptional functions of ERR alpha with IC50 = 0.021 mu M in a cell-based reporter gene assay and also decreased both the mRNA levels and the protein levels of ERR alpha and the downstream targets. This compound inhibited the proliferation and migration of breast cancer cells with high level of ERR alpha. Preliminary pharmacolcinetic studies suggested that it possessed a good pharmacokinetic profile with an oral bioavailability of 71.8%. The compounds may serve as novel small molecule probes for further validation of ERR alpha as a molecular target for anticancer drug development.

  DOI：

  10.1021/jm4003928

文献信息

• Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
  作者：Bo Chen、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2020.01.017

  日期：2020.3

  In this work, an interesting procedure for the synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent has been developed. With palladium as the catalyst and XPhos as the ligand under carbon monoxide pressure, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional group tolerance. Remarkably, this procedure also represents an example

  在这项工作中，从芳基叠氮化物和链烯基铝试剂合成α，β-不饱和酰胺的有趣方法已经被开发出来。以钯为催化剂，以XPhos为配体，在一氧化碳压力下，以良好的收率和良好的官能度耐受性分离出所需的α，β-不饱和酰胺。值得注意的是，该程序也代表了向异氰酸酯中添加有机金属试剂以合成α，β-不饱和酰胺的例子。
• Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α′-Amide Sulfoxonium Ylides from Azides
  作者：Yang Yuan、Bo Chen、Youcan Zhang、Xiao-Feng Wu

  DOI：10.1021/acs.joc.0c00273

  日期：2020.4.17

  The synthesis of α-carbonyl-α′-amide sulfoxonium ylides by Pd/C-catalyzed carbonylative transformation of azides with α-carbonyl sulfoxonium ylides has been studied. This method offers a direct approach to produce synthetically useful α-carbonyl-α′-amide sulfoxonium ylides in high efficiency. By using readily available substrates, 39 examples of products were prepared in good yields with outstanding

  研究了Pd / C催化的叠氮化物与α-羰基sulf氧基化羰基的羰基化反应合成α-羰基-α'-酰胺基ox的合成。该方法提供了直接方法，以高效地生产合成有用的α-羰基-α'-酰胺亚砜基。通过使用容易获得的底物，以高收率制备了39种产品实例，并具有出色的官能团相容性。还给出了将获得的内酯转化为相应的1，3-二羰基化合物的例子。