4-Chlorphenylacetylazid | 115601-14-4

• 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-Chlorphenylacetylazid
• 英文别名: 2-(4-chlorophenyl)acetyl azide；(4-chloro-phenyl)-acetyl azide；4-Chlor-phenylessigsaeure-azid
• CAS: 115601-14-4
• 化学式: C₈H₆ClN₃O
• 分子量: 195.608
• InChiKey: ILEPPDGEVCHFLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Chlorphenylacetylazid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.5h， 生成
  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：

  对氯苯乙酸乙酯 在 盐酸 、 乙醇 、 一水合肼 、 sodium nitrite 作用下， 生成 4-Chlorphenylacetylazid
  参考文献：
  名称：

  Curtius, Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 89, p. 500,512

  摘要：

  DOI：

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。
• Ruthenium-catalysed direct C–H amidation of 4-aryl-pyrrolo[2,3-<i>d</i>]pyrimidines with acyl/phosphoryl azides
  作者：Chenhong Pan、Chun He、Jiangrong Wang、Junyang Tang、Xingxian Zhang

  DOI：10.1039/d3ob01946b

  日期：——

  A ruthenium-catalysed arene ortho C–H amidation of 4-aryl-pyrrolo[2,3-d]pyrimidine derivatives with acyl azides or phosphoryl azides as the nitrogen sources toward C–N bond formation was developed. This protocol could offer a novel and direct approach to access a series of amidated and phosphoramidated pyrrolo[2,3-d]pyrimidine derivatives in moderate to good yields, thereby evading the general Curtius

  开发了钌催化的 4-芳基吡咯并[2,3- d ]嘧啶衍生物与酰基叠氮化物或磷酰叠氮化物作为氮源形成 C-N 键的芳烃邻位C-H 酰胺化反应。该方案可以提供一种新颖且直接的方法，以中等至良好的产率获得一系列酰胺化和磷酰胺化吡咯并[2,3 -d ]嘧啶衍生物，从而避免一般的Curtius重排。该方案具有显着的官能团耐受性和单步过程，仅释放无害的分子氮作为副产物。
• Kathodische Reduktion von S�ureaziden Elektrolytische Untersuchungen an Vinylaziden, 8. Mitt.
  作者：Dierk Knittel

  DOI：10.1007/bf00810418

  日期：1988.4
• Curtius, Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 89, p. 500,512
  作者：Curtius

  DOI：——

  日期：——
• Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones
  作者：Shrenik K. Shah、Conrad P. Dorn、Paul E. Finke、Jeffrey J. Hale、William K. Hagmann、Karen A. Brause、Gilbert O. Chandler、Amy L. Kissinger、Bonnie M. Ashe

  DOI：10.1021/jm00099a003

  日期：1992.10

  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.