1,4-dibenzyl-1H-imidazol-2-ylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dibenzyl-1H-imidazol-2-ylamine
• 英文别名: 1,4-Dibenzylimidazol-2-amine
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: FJXBOQAAZWRWBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯丙酸乙酯 在 N,N-二甲基丙烯基脲 、 三氢化钐 、 1,2-二碘乙烷 、 trizyl azide 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,4-dibenzyl-1H-imidazol-2-ylamine
  参考文献：
  名称：

  Synthesis of Marine Alkaloids Isonaamine A, Dorimidazole A, and Preclathridine A. Iminophosphorane-Mediated Preparation of 2-Amino-1,4-disubstituted Imidazoles from α-Azido Esters

  摘要：

  DOI：

  10.1021/jo9819382

文献信息

• Efficient One-Pot, Two-Step, Microwave-Assisted Procedure for the Synthesis of Polysubstituted 2-Aminoimidazoles
  作者：Denis S. Ermolat'ev、Eugene V. Babaev、Erik V. Van der Eycken

  DOI：10.1021/ol062421c

  日期：2006.12.1

  A microwave-assisted, one-pot, two-step protocol was developed for the construction of polysubstituted 2-aminoimidazoles. This process involves the sequential formation of imidazo[1,2-a]pyrimidinium salts from readily available 2-aminopyrimidines and alpha-bromocarbonyl compounds, followed by opening of the pyrimidine ring with hydrazine. [reaction: see text]

  开发了微波辅助的一锅两步操作规程，用于构建多取代的2-氨基咪唑。该过程涉及由容易获得的2-氨基嘧啶和α-溴羰基化合物顺序形成咪唑并[1,2-a]嘧啶鎓盐，然后用肼打开嘧啶环。[反应：看文字]
• A Concise Microwave-Assisted Synthesis of 2-Aminoimidazole Marine Sponge Alkaloids of the Isonaamines Series
  作者：E. Babaev、E. Van der Eycken、D. Ermolat’ev、V. Alifanov、V. Rybakov

  DOI：10.1055/s-2008-1078444

  日期：——

  A short and efficient route to 1,4-substituted 2-aminoimidazole alkaloids starting from the easily accessible 2-alkylaminopyrimidines and α-bromo aldehydes is reported. The formation of the intermediate imidazo[1,2-a]pyrimidinium salts and subsequent cleavage were facilitated by microwave irradiation. Marine sponge alkaloids preclathridines A, C and isonaamines A, C, D were obtained in high yields using the optimized one-pot two-step procedure.

  本研究报道了从容易获得的 2-烷基氨基嘧啶和δ-溴醛出发，制备 1,4 代 2-氨基咪唑生物碱的简短而有效的路线。微波辐照促进了中间体咪唑并[1,2-a]嘧啶盐的形成和随后的裂解。利用优化的一锅两步法，高产率地获得了海洋海绵生物碱 preclathridines A、C 和异纳胺 A、C、D。
• A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines
  作者：Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo8008758

  日期：2008.9.1

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.
• A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation
  作者：Gianpaolo Chiriano、Angela De Simone、Francesca Mancini、Daniel I. Perez、Andrea Cavalli、Maria Laura Bolognesi、Giuseppe Legname、Ana Martinez、Vincenza Andrisano、Paolo Carloni、Marinella Roberti

  DOI：10.1016/j.ejmech.2011.12.016

  日期：2012.2

  In this work, we report a rational structure-based approach aimed at the discovery of new 2-aminoimidazoles as beta-secretase inhibitors. Taking advantage of a microwave-assisted synthetic protocol, a small library of derivatives was obtained and biologically evaluated. Two compounds showed promising activities in both enzymatic and cellular assays. Moreover, one of them exhibited the capability to cross the blood brain barrier as assessed by the parallel artificial membrane permeability assay. (C) 2011 Elsevier Masson SAS. All rights reserved.