[3-(2,4-dichlorophenyl)aziridin-2-yl]-phenylmethanone | 1555972-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(2,4-dichlorophenyl)aziridin-2-yl]-phenylmethanone
• CAS: 1555972-04-7
• 化学式: C₁₅H₁₁Cl₂NO
• 分子量: 292.164
• InChiKey: PXSSJEOFHWDUCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  39.01
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [3-(2,4-dichlorophenyl)aziridin-2-yl]-phenylmethanone 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94%的产率得到2-(2,4-dichlorophenyl)-5-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。
• Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines
  作者：Heshmat Samimi、Bohari Yamin、Fatemeh Saberi

  DOI：10.1055/s-0034-1379029

  日期：——

  A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc)(2)O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.