N-(2-chlorobenzyl)-(2-pyrimidyl)amine | 23676-58-6

• 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-(2-chlorobenzyl)-(2-pyrimidyl)amine
• 英文别名: 2-(o-Chlorbenzylamino)pyrimidin；N-(2-chlorobenzyl)pyrimidin-2-amine；(2-chloro-benzyl)-pyrimidin-2-yl-amine；N-[(2-chlorophenyl)methyl]pyrimidin-2-amine
• CAS: 23676-58-6
• 化学式: C₁₁H₁₀ClN₃
• mdl: MFCD00453213
• 分子量: 219.673
• InChiKey: BHLMHANVTWPPBT-UHFFFAOYSA-N

物化性质

• 沸点：
  391.9±44.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-溴-3-苯基丙醛 、 N-(2-chlorobenzyl)-(2-pyrimidyl)amine 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以11%的产率得到4-benzyl-1-(2-chlorobenzyl)-1H-imidazol-2-amine
  参考文献：
  名称：

  A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.12.016
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 邻氯苄醇 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以83%的产率得到N-(2-chlorobenzyl)-(2-pyrimidyl)amine
  参考文献：
  名称：

  用于选择性合成取代的嘧啶和氨基嘧啶的新型可回收催化剂

  摘要：

  公认配体在选择性合成和催化中起关键作用。采用现代方法合成并充分表征了新型吡啶基三嗪骨架配体，相应的催化剂SBA-15@TZP-Ir和SBA-15@TZP-Ru。所得催化剂在以高产率选择性合成有用的取代的嘧啶和氨基嘧啶时显示出高催化活性。此外，SBA-15@TZP-Ir 和 SBA-15@TZP-Ru 可以轻松回收五次用于转化，并进行了初步机制探索以更好地研究这些反应。 图形概要 合成、表征了介孔二氧化硅负载的铱和钌催化剂（SBA-15@TZP-Ir，SBA-15@TZP-Ru），并在合成有用的取代嘧啶和氨基嘧啶时表现出高催化活性，收率高。

  DOI：

  10.1007/s10562-022-04153-6

文献信息

• Structure-dependent tautomerization induced catalyst-free autocatalyzed N-alkylation of heteroaryl amines with alcohols
  作者：Shuangyan Li、Xiaohui Li、Qiang Li、Qiaochao Yuan、Xinkang Shi、Qing Xu

  DOI：10.1039/c4gc02542c

  日期：——

  Catalyst-free autocatalyzedN-alkylation of heteroarylamines with alcohols is achieved by tautomerization-induced ready generation of carbonyl intermediates from alcoholsviaTM-free MPV–O reaction.

  无需催化剂的自催化杂环胺与醇的N-烷基化是通过醇经酮互变引发的易生成羰基中间体实现的，通过无铁催化的MPV-O反应。
• Manganese Dioxide Catalyzed<i>N-</i>Alkylation of Sulfonamides and Amines with Alcohols under Air
  作者：Xiaochun Yu、Chuanzhi Liu、Lan Jiang、Qing Xu

  DOI：10.1021/ol202582c

  日期：2011.12.2

  By simply running the reactions under air and solvent-free conditions using catalytic amounts of manganese dioxide, a practical and efficient N-allrylation method for a variety of sulfonamides and amines using alcohols as green alkylating reagents was developed.
• 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.
• Novel Recyclable Catalysts for Selective Synthesis of Substituted Perimidines and Aminopyrimidines
  作者：Bo Zhang、Jiahao Li、Haiyan Zhu、Xiao-Feng Xia、Dawei Wang

  DOI：10.1007/s10562-022-04153-6

  日期：——

  It was accepted ligands played key role for selective synthesis and catalysis. A novel pyridinyltriazine skeleton ligand, the corresponding catalysts SBA-15@TZP-Ir and SBA-15@TZP-Ru were synthesized and fully characterized by modern methods. The resulting catalysts showed high catalytic activity in selective synthesis of useful substituted perimidines and aminopyrimidines in high yields. Additionally

  公认配体在选择性合成和催化中起关键作用。采用现代方法合成并充分表征了新型吡啶基三嗪骨架配体，相应的催化剂SBA-15@TZP-Ir和SBA-15@TZP-Ru。所得催化剂在以高产率选择性合成有用的取代的嘧啶和氨基嘧啶时显示出高催化活性。此外，SBA-15@TZP-Ir 和 SBA-15@TZP-Ru 可以轻松回收五次用于转化，并进行了初步机制探索以更好地研究这些反应。 图形概要 合成、表征了介孔二氧化硅负载的铱和钌催化剂（SBA-15@TZP-Ir，SBA-15@TZP-Ru），并在合成有用的取代嘧啶和氨基嘧啶时表现出高催化活性，收率高。