N,1-dibenzyl-4,5-dihydro-1H-imidazol-2-amine | 1434639-78-7

• 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: N,1-dibenzyl-4,5-dihydro-1H-imidazol-2-amine
• 英文别名: 1-Benzyl-2-(benzylamino)-4,5-dihydro-1H-imidazole；N,1-dibenzyl-4,5-dihydroimidazol-2-amine
• CAS: 1434639-78-7
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: UDTIJQDUEHVVDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲酸 、 N,1-dibenzyl-4,5-dihydro-1H-imidazol-2-amine 以 水 、 乙腈 为溶剂， 以197 mg的产率得到N,1-dibenzyl-4,5-dihydroimidazol-2-amine;formic acid
  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
• 作为产物：
  描述：

  苯甲胺,N-(2-叠氮乙基)- 在 (n-Bu)₂PhP polystyrene 作用下， 以 甲苯 为溶剂， 反应 0.41h， 生成 N,1-dibenzyl-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

• NOVEL GUANIDINE DERIVATIVES AND THEIR MEDICAL USE
  申请人：Sorensen Ulrik Svane

  公开号：US20090099208A1

  公开（公告）日：2009-04-16

  This invention relates to novel guanidine derivatives useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及一种新型胍基衍生物，可用作小电导钙激活钾通道（SK通道）的调节剂。在其他方面，本发明涉及使用这些化合物的方法进行治疗，以及包括本发明化合物的制药组合物。
• US8048877B2
  申请人：——

  公开号：US8048877B2

  公开（公告）日：2011-11-01
• [EN] NOVEL GUANIDINE DERIVATIVES AND THEIR MEDICAL USE<br/>[FR] NOUVEAUX DÉRIVÉS DE GUANIDINE ET UTILISATION MÉDICALE DE CEUX-CI
  申请人：NEUROSEARCH AS

  公开号：WO2007110363A1

  公开（公告）日：2007-10-04

  [EN] This invention relates to novel guanidine derivatives useful as modulators of small-conductance calcium-activated potassium channels (SK channels). In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.
  [FR] Cette invention concerne de nouveaux dérivés de guanidine utiles en tant que modulateurs des canaux potassiques activés par le calcium de faible conductance (canaux SK). Dans d'autres aspects, l'invention concerne l'utilisation de ces composés dans un procédé de thérapie ainsi que des compositions pharmaceutiques comprenant les composés de l'invention.
• 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.