1-(2-氨基苯基)-2-氮杂环丁酮 | 682341-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 1-(2-氨基苯基)-2-氮杂环丁酮
• 英文名称: N-(2-aminophenyl)-2-azetidinone
• 英文别名: 1-(2-Aminophenyl)azetidin-2-one
• CAS: 682341-17-9
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: PVBIYRKDWMPTLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基苯基)-2-氮杂环丁酮 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以154 mg的产率得到1,3,4,5-四氢-苯并[B][1,4]二氮杂革-2-酮
  参考文献：
  名称：

  Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process

  摘要：

  A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of beta-Iactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate beta-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.

  DOI：

  10.1021/ja038565t
• 作为产物：
  描述：

  2-氮杂环丁酮 、 2-碘苯胺 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以95%的产率得到1-(2-氨基苯基)-2-氮杂环丁酮
  参考文献：
  名称：

  Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process

  摘要：

  A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of beta-Iactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate beta-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.

  DOI：

  10.1021/ja038565t

文献信息

• [EN] PYRIMIDINE DERIVATIVES AS HIV INTEGRASE INHIBITORS<br/>[FR] DERIVES DE LA PYRIMIDINE, INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2007064619A1

  公开（公告）日：2007-06-07

  [EN] The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV. Formula (I)
  [FR] L'invention porte sur une série de composés bicycliques de pyrimidinone de formule (I) qui inhibent l'intégrase du VIH et empêchent l'intégration du virus à l'ADN humain. Cette action rend ces composés utiles pour traiter les infections par le VIH et le SIDA. L'invention porte également sur des préparations pharmaceutiques et des méthodes de traitement des patients infectés par le VIH.
• Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process
  作者：Artis Klapars、Sean Parris、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/ja038565t

  日期：2004.3.1

  A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of beta-Iactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate beta-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.