2-azido-N-naphthalen-2-yl-N-phenylacetamide | 1448363-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-azido-N-naphthalen-2-yl-N-phenylacetamide
• CAS: 1448363-18-5
• 化学式: C₁₈H₁₄N₄O
• 分子量: 302.335
• InChiKey: LWQUEFWGSWJYTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-naphthalen-2-yl-N-phenylacetamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以70%的产率得到4-phenylbenzo[f]quinoxalin-3(4H)-one
  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：

  N-苯基-2-萘胺 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-naphthalen-2-yl-N-phenylacetamide
  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.