2-azido-N-(4-bromophenyl)-N-methylacetamide | 1448363-09-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-azido-N-(4-bromophenyl)-N-methylacetamide
• CAS: 1448363-09-4
• 化学式: C₉H₉BrN₄O
• 分子量: 269.101
• InChiKey: GMXOBLACCAIVBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 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：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-N-(4-bromophenyl)-N-methylacetamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到6-溴-1-甲基喹喔啉-2(1H)-酮
  参考文献：
  名称：

  Photoinduced and N-Bromosuccinimide-Mediated Cyclization of 2-Azido-N-phenylacetamides

  摘要：

  An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1,2'-imidazol]-4'-cones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2'-imidazol]-4'cones are obtained as the main products when the substrates bear electron-donating groups at the para-position.

  DOI：

  10.1021/ol401338e
• 作为产物：
  描述：

  4-溴-N-甲基苯胺 在 sodium azide 、 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 3.5h， 生成 2-azido-N-(4-bromophenyl)-N-methylacetamide
  参考文献：
  名称：

  Photoinduced and N-Bromosuccinimide-Mediated Cyclization of 2-Azido-N-phenylacetamides

  摘要：

  An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1,2'-imidazol]-4'-cones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2'-imidazol]-4'cones are obtained as the main products when the substrates bear electron-donating groups at the para-position.

  DOI：

  10.1021/ol401338e

文献信息

• Photoinduced and <i>N</i>-Bromosuccinimide-Mediated Cyclization of 2-Azido-<i>N</i>-phenylacetamides
  作者：Zhan-Shan Li、Wei-Xia Wang、Ji-Dong Yang、Yue-Wei Wu、Wei Zhang

  DOI：10.1021/ol401338e

  日期：2013.8.2

  An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1,2'-imidazol]-4'-cones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2'-imidazol]-4'cones are obtained as the main products when the substrates bear electron-donating groups at the para-position.