2-azido-5-methylbenzylamine | 146954-05-4

• 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: 2-azido-5-methylbenzylamine
• 英文别名: (2-Azido-5-methylphenyl)methanamine
• CAS: 146954-05-4
• 化学式: C₈H₁₀N₄
• 分子量: 162.194
• InChiKey: JJGALMFYBATEOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-5-methylbenzylamine 在 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 15.0h， 生成 Bis(2-azidobenzyl)(2-azido-5-methylbenzyl)amine N-oxide
  参考文献：
  名称：

  Tripod-Tripod Coupling of Triazides with Triphosphanes. The Synthesis, Characterization, and Stability in Solution of New Cage Compounds: Chiral Macrobicyclic Triphosphazides

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2558::aid-chem2558>3.0.co;2-3
• 作为产物：
  描述：

  2-azido-5-methylbenzyl alcohol 在 氯化亚砜 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-azido-5-methylbenzylamine
  参考文献：
  名称：

  Synthetic applications of bis(iminophosphoranes). One-pot preparation of rigid bicyclic guanidines

  摘要：

  A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.

  DOI：

  10.1021/jo00059a015

文献信息

• One-pot and regioselective synthesis of polysubstituted 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by sequential Ugi/Staudinger/aza-Wittig reaction
  作者：Jun Xiong、Xiao Wei、Yu-Chen Wan、Ming-Wu Ding

  DOI：10.1016/j.tet.2019.01.014

  日期：2019.2

  efficient one-pot and regioselective synthesis of 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi reactions of 2-azidobenzylamines, aldehydes, acids (or α-keto acids) and isocyanides produced the azide intermediates, which were then treated with tributylphosphine or triphenylphosphine to give polysubstituted 3,4-dihydroquinazolines

  已经开发了通过Ugi / Staudinger / aza-Wittig序列有效地一锅法和区域选择性合成3,4-二氢喹唑啉和4,5-二氢-3 H -1,4-苯并二氮杂-3-酮的方法。2-叠氮基苄胺，醛，酸（或α-酮酸）和异氰酸酯的Ugi反应生成叠氮化物中间体，然后将其用三丁基膦或三苯基膦处理，得到多取代的3,4-二氢喹唑啉或4,5-二氢-3 H通过串联Stander / Aza-Wittig反应，中度至良好产率的-1,4-苯并二氮杂-3-酮。
• One-pot and regioselective synthesis of 3,4-dihydroquinazolines by Sequential Ugi/Staudinger/aza-Wittig reaction starting from functionalized isocyanides
  作者：Jun Xiong、Xiao Wei、Yan-Mei Yan、Ming-Wu Ding

  DOI：10.1016/j.tet.2017.08.011

  日期：2017.9

  new one-pot and regioselective synthesis of 3,4-dihydroquinazolines by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi-type reaction of 2-azidobenzylisocyanide, aldehyde, secondary amine and acid produced an azide intermediate, which was then treated with triphenylphosphine to give 3,4-dihydroquinazolines regioselectively in good overall yields by Staudinger/aza-Wittig reaction at room

  已经开发了一种新的由Ugi / Staudinger / aza-Wittig序列进行的一锅法和区域选择性合成3,4-二氢喹唑啉。2-叠氮基苄基异氰酸酯，醛，仲胺和酸的Ugi型反应生成叠氮化物中间体，然后将其用三苯基膦处理，在室温下通过Staudinger / aza-Wittig反应以良好的总收率选择性地以良好的总收率生成3,4-二氢喹唑啉。
• Intramolecular [2 + 2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines
  作者：Mateo Alajarín、Pedro Molina、Angel Vidal、Fulgencio Tovar

  DOI：10.1016/s0040-4020(97)00855-7

  日期：1997.9

  Azeto[2,1-b]quinazolines 5 have been prepared by the novel intramolecular [2 + 2] cycloaddition reaction of ketenimines with imines. The applicability and limitations of the synthetic methodology, and explorations on the reactivity of compounds 5 are discussed. (C) 1997 Elsevier Science Ltd.
• Synthetic applications of bis(iminophosphoranes). One-pot preparation of rigid bicyclic guanidines
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal

  DOI：10.1021/jo00059a015

  日期：1993.3

  A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.
• Tripod-Tripod Coupling of Triazides with Triphosphanes. The Synthesis, Characterization, and Stability in Solution of New Cage Compounds: Chiral Macrobicyclic Triphosphazides
  作者：Mateo Alajarín、Antonia López-Lázaro、Angel Vidal、José Berná

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2558::aid-chem2558>3.0.co;2-3

  日期：1998.12.4