2-亚氨基-1-苄基-5-甲氧基吡咯烷 | 1005340-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-亚氨基-1-苄基-5-甲氧基吡咯烷
• 英文名称: 2-imino-1-benzyl-5-methoxypyrrolidine
• 英文别名: 1-Benzyl-5-methoxypyrrolidin-2-imine；1-benzyl-5-methoxypyrrolidin-2-imine
• CAS: 1005340-40-8
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: XPVOFUHNJDVDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  36.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(benzylamino)pentanedinitrile 、 sodium methylate 以 甲醇 为溶剂， 反应 24.0h， 生成 2-亚氨基-1-苄基-5-甲氧基吡咯烷
  参考文献：
  名称：

  Novel synthesis of 2-aminopentanedinitriles from 2-(bromomethyl)aziridines and their transformation into 2-imino-5-methoxypyrrolidines and 5-methoxypyrrolidin-2-ones

  摘要：

  1-Arylmethyl-2-(bromomethyl)aziridines were transformed into 2-[N-(arylmethyl)amino]pentanedinitriles upon treatment with an excess of potassium cyanide in DMSO through an unprecedented and peculiar reaction mechanism, involving base-induced ring opening of intermediate 2-(cyanomethyl)aziridines into allylamines, followed by migration of the double bond out of the conjugation towards aldimines via enamine intermediates. The resulting aminopentanedinitriles, served as substrates for the synthesis of novel 2-imino-5-methoxypyrrolidines upon treatment with sodium methoxide in methanol, which were either acetylated at the free imino group to afford the more stable N-acetylimino derivatives or hydrolyzed towards the corresponding synthetically relevant 5-methoxypyrrolidin-2-ones. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.116

文献信息

• Novel synthesis of 2-aminopentanedinitriles from 2-(bromomethyl)aziridines and their transformation into 2-imino-5-methoxypyrrolidines and 5-methoxypyrrolidin-2-ones
  作者：Matthias D'hooghe、Andries Van Nieuwenhove、Willem Van Brabandt、Mario Rottiers、Norbert De Kimpe

  DOI：10.1016/j.tet.2007.03.116

  日期：2008.2

  1-Arylmethyl-2-(bromomethyl)aziridines were transformed into 2-[N-(arylmethyl)amino]pentanedinitriles upon treatment with an excess of potassium cyanide in DMSO through an unprecedented and peculiar reaction mechanism, involving base-induced ring opening of intermediate 2-(cyanomethyl)aziridines into allylamines, followed by migration of the double bond out of the conjugation towards aldimines via enamine intermediates. The resulting aminopentanedinitriles, served as substrates for the synthesis of novel 2-imino-5-methoxypyrrolidines upon treatment with sodium methoxide in methanol, which were either acetylated at the free imino group to afford the more stable N-acetylimino derivatives or hydrolyzed towards the corresponding synthetically relevant 5-methoxypyrrolidin-2-ones. (c) 2007 Elsevier Ltd. All rights reserved.