1-butyl-3-(p-nitrophenyl)-4-vinyl-1,3-diazepin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-butyl-3-(p-nitrophenyl)-4-vinyl-1,3-diazepin-2-one
• 英文别名: 1-Butyl-4-ethenyl-3-(4-nitrophenyl)-1,3-diazepan-2-one
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: SEJWMULNEQALDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸对硝基苯 、 N-butyl-2-vinylpyrrolidine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 作用下， 以 四氢呋喃 为溶剂， 40.0 ℃ 、34.47 kPa 条件下， 反应 12.0h， 以70%的产率得到1-butyl-3-(p-nitrophenyl)-4-vinyl-1,3-diazepin-2-one
  参考文献：
  名称：

  Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates

  摘要：

  The first palladium-catalyzed ring-expansion reaction of 2-vinylpyrrolidines with aryl isocyanates to form seven-membered ring heterocycles is described. This regioselective reaction requires 5 mol % of Pd-2(dba)(3).CHCl3 and 10 mol % of dppp at 40-60 degreesC in THF and results in the formation of 1,3-diazepin-2-ones in good isolated yields. When Pd(OAc)(2) and PPh3 were utilized in the reaction, an intramolecular hydrogen migration occurs resulting in the formation of conjugated diene derivatives of urea.

  DOI：

  10.1021/jo020526x

文献信息

• Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates
  作者：Hai-Bing Zhou、Howard Alper

  DOI：10.1021/jo020526x

  日期：2003.5.1

  The first palladium-catalyzed ring-expansion reaction of 2-vinylpyrrolidines with aryl isocyanates to form seven-membered ring heterocycles is described. This regioselective reaction requires 5 mol % of Pd-2(dba)(3).CHCl3 and 10 mol % of dppp at 40-60 degreesC in THF and results in the formation of 1,3-diazepin-2-ones in good isolated yields. When Pd(OAc)(2) and PPh3 were utilized in the reaction, an intramolecular hydrogen migration occurs resulting in the formation of conjugated diene derivatives of urea.