N,1-bis(4-methoxybenzyl)-4,5-dihydro-1H-imidazol-2-amine | 1434640-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,1-bis(4-methoxybenzyl)-4,5-dihydro-1H-imidazol-2-amine
• 英文别名: N,1-bis[(4-methoxyphenyl)methyl]-4,5-dihydroimidazol-2-amine
• CAS: 1434640-29-5
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: PEXGLOAQSAZSBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三丁基膦 作用下， 反应 0.33h， 以208 mg的产率得到N,1-bis(4-methoxybenzyl)-4,5-dihydro-1H-imidazol-2-amine
  参考文献：
  名称：

  Synthesis of Differentially Substituted 2-Aminoimidazolidines via a Microwave-Assisted Tandem Staudinger/Aza-Wittig Cyclization

  摘要：

  A new route for the construction of 2-aminoimidazolidines including analogues of the alpha(2) adrenergic agonist drug clonidine is elaborated. The key step is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate (formed by the reaction of beta-amino azide and isocyanate) upon treatment with Bu3P or polymer-supported phosphine reagent, allowing the introduction of various substituents at the N1 and the 2-amino function. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald-Hartwig protocol leading to bicyclic guanidines has been elaborated.

  DOI：

  10.1021/jo400481b

文献信息

• Synthesis of Differentially Substituted 2-Aminoimidazolidines via a Microwave-Assisted Tandem Staudinger/Aza-Wittig Cyclization
  作者：Rakesh Kumar、Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo400481b

  日期：2013.6.7

  A new route for the construction of 2-aminoimidazolidines including analogues of the alpha(2) adrenergic agonist drug clonidine is elaborated. The key step is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate (formed by the reaction of beta-amino azide and isocyanate) upon treatment with Bu3P or polymer-supported phosphine reagent, allowing the introduction of various substituents at the N1 and the 2-amino function. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald-Hartwig protocol leading to bicyclic guanidines has been elaborated.