N-butyl-2-vinylpyrrolidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-butyl-2-vinylpyrrolidine
• 英文别名: 1-Butyl-2-ethenylpyrrolidine
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: VSPRONCWCLRTHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对甲氧基苯异氰酸酯 、 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， 60.0 ℃ 、34.47 kPa 条件下， 反应 48.0h， 以11%的产率得到1-butyl-3-(p-methoxyphenyl)-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

• Regioselective and enantioselective synthesis of seven-membered ring cyclic arylguanidine and urea derivatives
  作者：Hai-Bing Zhou、Howard Alper

  DOI：10.1016/j.tet.2003.10.088

  日期：2004.1

  Cycloaddition reaction of 2-vinylpyrrolidines with carbodiimides in the presence of palladium acetate and dpppentane affords seven-membered ring cyclic arylguanidines in good yields and conversions. When 1-butyl-4-methyl-2-vinylpyrrolidine 1c was used as a mixture of trans and cis isomers in a 4:1 ratio, and reacted with bis(2-chlorophenyl)carbodiimide 2a, high stereoselectivity was achieved and only

  2-乙烯基吡咯烷与碳二亚胺在乙酸钯和dpppentane的存在下进行环加成反应，可提供良好的收率和转化率的七元环芳基胍。当1-丁基-4-甲基-2-乙烯基吡咯1C用作的混合物反式和CIS的4种异构体：1的比例，并与双（2-氯苯基）碳二亚胺反应2a中，高立体选择性达到并且仅反得到七元环状胍。吡咯烷环的4-位上的甲基和碳二亚胺的邻位上的氯取代基可能是有利于反式异构体的产物比率提高的原因。
• 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.