ethyl 3-(2-bromophenylamino)-2-methylenebutanoate | 1392285-99-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 3-(2-bromophenylamino)-2-methylenebutanoate
• 英文别名: Ethyl 3-(2-bromoanilino)-2-methylidenebutanoate；ethyl 3-(2-bromoanilino)-2-methylidenebutanoate
• CAS: 1392285-99-2
• 化学式: C₁₃H₁₆BrNO₂
• 分子量: 298.18
• InChiKey: VRSWRWPASIVFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕各酸乙酯 、 N-(2-bromophenyl)hydroxylamine 在 iron(II) chloride tetrahydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以78%的产率得到ethyl 3-(2-bromophenylamino)-2-methylenebutanoate
  参考文献：
  名称：

  Direct Synthesis of β-Alkyl N-Aryl Aza Baylis–Hillman Adducts via Nitroso-Ene Reaction

  摘要：

  A new approach for the direct Fe-catalyzed synthesis of beta-alkyl N-aryl aza Baylis-Hillman (ABH) adducts is reported. This approach involves the formation of a C-N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction, which converts allyl esters and carbonyl compounds to novel ABH adducts. A variety of arylhydroxylamines reacted with esters, aldehydes, ketone, and nitriles to yield the corresponding products in moderate to excellent yields.

  DOI：

  10.1021/jo301266f

文献信息

• Direct Synthesis of β-Alkyl <i>N</i>-Aryl Aza Baylis–Hillman Adducts via Nitroso-Ene Reaction
  作者：Siva Murru、August A. Gallo、Radhey S. Srivastava

  DOI：10.1021/jo301266f

  日期：2012.8.17

  A new approach for the direct Fe-catalyzed synthesis of beta-alkyl N-aryl aza Baylis-Hillman (ABH) adducts is reported. This approach involves the formation of a C-N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction, which converts allyl esters and carbonyl compounds to novel ABH adducts. A variety of arylhydroxylamines reacted with esters, aldehydes, ketone, and nitriles to yield the corresponding products in moderate to excellent yields.