(4-Bromophenyl)(3-phenylaziridin-2-yl)methanone | 72997-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-Bromophenyl)(3-phenylaziridin-2-yl)methanone
• 英文别名: (4-bromophenyl)-(3-phenylaziridin-2-yl)methanone
• CAS: 72997-91-2
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: QJYYZTSLYWQCNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  39
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-Bromophenyl)(3-phenylaziridin-2-yl)methanone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以84%的产率得到5-(4-bromophenyl)-2-phenyloxazole
  参考文献：
  名称：

  N-Bromosuccinimide as a Brominating Agent for the Transformation of N-H (or N-Benzyl) Ketoaziridines into Oxazoles

  摘要：

  A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.

  DOI：

  10.1055/s-0034-1380518

文献信息

• Synthesis of polysubstituted pyrroles via [3 + 2]-annulation of aziridines and β-nitroalkenes under aerobic conditions
  作者：Shaoyin Wang、Xiancui Zhu、Zhuo Chai、Shaowu Wang

  DOI：10.1039/c3ob42324g

  日期：——

  Polysubstituted pyrroles were regioselectively synthesized in moderate to good yields via the copper acetate-catalyzed [3 + 2] annulation reaction of readily accessible aziridines and nitroalkenes. This reaction was proposed to proceed through a key azomethine ylide intermediate generated by selective C–C bond cleavage of the aziridine followed by annulation with nitroalkenes under aerobic conditions

  多聚取代的吡咯通过乙酸铜催化的易获得的氮丙啶和硝基烯烃的[3 + 2]环化反应，以中等至良好的产率进行区域选择性合成。该反应被提议通过一个关键的偶氮甲叶立德中间体进行，该中间体由氮丙啶的选择性C-C键裂解产生，然后在有氧条件下用硝基烯烃环化。
• Copper-catalyzed cascade approach to 1,3-diazabicyclo[3.1.0]hex-3-enes from aziridines and ethyl diazoacetate
  作者：Yuanxun Zhu、Shaoyin Wang、Shan Wen、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tetlet.2010.07.026

  日期：2010.9

  An efficient and general synthesis of 1,3-diazabicyclo[3.1.0]hex-3-enes via the copper-catalyzed cascade reaction of aziridines with ethyl diazoacetate is described.

  描述了一种通过铜催化的氮丙啶与重氮乙酸乙酯的级联反应有效而一般地合成1,3-二氮杂双环[3.1.0]己-3-烯的方法。
• Synthesis of Highly Substituted 2-Imidazolines through a Three-Component Coupling Reaction
  作者：Yong-Min Liang、Yao Han、Yong-Xin Xie、Lian-Biao Zhao、Ming-Jin Fan

  DOI：10.1055/s-2007-1000818

  日期：2008.1

  A simple strategy for the synthesis of highly substituted 2-imidazolines starting from terminal alkynes, sulfonyl azides, and N-unsubstituted aziridines via two steps with high regioselectivity is described.

  描述了一种从末端炔烃、磺酰叠氮化物和 N-未取代的氮丙啶开始，通过两个具有高区域选择性的步骤合成高度取代的 2-咪唑啉的简单策略。