(4-Methoxy-phenyl)-acetyl azide | 87721-45-7

• 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-Methoxy-phenyl)-acetyl azide
• 英文别名: 4-Methoxybenzylcarbonyl azide；2-(4-methoxyphenyl)acetyl azide
• CAS: 87721-45-7
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: UCRHHOFYNYPRNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-Methoxy-phenyl)-acetyl azide 在 4-二甲氨基吡啶 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 25.5h， 生成 4-[3,3-Diethyl-1-(4-methoxy-benzylcarbamoyl)-4-oxo-azetidin-2-yloxy]-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (4-Methoxy-phenyl)-acetyl azide
  参考文献：
  名称：

  一种GLUT1抑制剂、虚拟筛选方法及应用

  摘要：

  本发明涉及一种GLUT1抑制剂、虚拟筛选方法及应用，所述GLUT1抑制剂的结构如式(Ⅰ)所示的系列化合物及其衍生物中的一种或几种：其中，X为单键或者C1‑C6亚烷基；R1为取代或未取代的C3‑C10环烷基或者取代或未取代的C3‑C10杂环烷基；R2为C1‑C6烷氧基，C1‑C6烷硫基，C1‑C6烷烯基，取代或未取代的C3‑C10环烷基，取代或未取代的C3‑C10杂环烷基、取代或未取代的芳基，或者取代或未取代的芳香杂环。具有更好的GLUT1抑制活性和更为优秀的ADMET性质，具有非常好的应用前景，为后续GLUT1抑制剂的设计提供研究基础。

  公开号：

  CN115286592A

文献信息

• Facile preparation of protected benzylic and heteroarylmethyl amines via room temperature Curtius rearrangement
  作者：Matthew L. Leathen、Emily A. Peterson

  DOI：10.1016/j.tetlet.2010.03.101

  日期：2010.5

  Curtius rearrangement of phenyl and heteroaryl acetic acids is described. We have developed a protocol for room temperature Curtius rearrangement in MeOH or CHCl3 that provides an improvement over standard conditions, avoiding the use of additives or heat. This room temperature optimization of the Curtius rearrangement prevents the formation of side products often observed with benzylic acids, allowing

  描述了用于形成酰基叠氮化物以及随后的苯基和杂芳基乙酸的Curtius重排的分步室温过程。我们已经开发出了在MeOH或CHCl 3中进行室温Curtius重排的规程，该规程比标准条件有所改进，避免了使用添加剂或加热。Curtius重排的这种室温优化可防止形成通常在苯甲酸中观察到的副产物，从而可以使用各种苯甲基和杂芳基甲基胺。
• Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones
  作者：Kevin M. Oberg、Ernest E. Lee、Tomislav Rovis

  DOI：10.1016/j.tet.2009.02.021

  日期：2009.6

  A highly regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of terminal alkynes with a variety of isocyanates to provide 2- and 4-pyridones has been developed. This reaction proceeds in good to excellent yields and overcomes the problem of dimerization and trimerization through the use of phosphoramidite ligands. A CO migration in the metallacycle is proposed to account for the formation of 4-pyridone. (C) 2009 Elsevier Ltd. All rights reserved.
• Trimethylsilyl azide-promoted acid-amine coupling: A facile one-pot route to amides from carboxylic acids and amines
  作者：Yellaiah Tangella、Jay Prakash Soni、Nagula Shankaraiah、Diana Abril、Manda Sathish

  DOI：10.24820/ark.5550190.p011.914

  日期：——