N-(2-adamantyl)-2-azidoacetamide | 1093981-73-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-adamantyl)-2-azidoacetamide
• CAS: 1093981-73-7
• 化学式: C₁₂H₁₈N₄O
• 分子量: 234.301
• InChiKey: YBQOZFPTIJQPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.86
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-adamantyl)-2-azidoacetamide 、 3,5-dimethyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine 在 copper(I) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以87%的产率得到2,2-{4,4-[(3,5-dimethyladamantan-1-ylazanediyl)-bis(methylene)]bis(1H-1,2,3-triazole-4,1-diyl)}bis[N-(adamantan-2-yl)acetamide]
  参考文献：
  名称：

  N,N-Di(prop-2-yn-1-yl)adamantan-1-amines in 1,3-Dipolar Cycloaddition Reactions with Azide-Containing Pharmacophores

  摘要：

  A synthetic approach to combining pharmacophore ligands with an aminoadamantyl-containing spacer based on a copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of N,N-di(prop-2-yne-1-yl)adamantan-1-amines and azido-containing carbazole, tetrahydrocarbazole, phenothiazine and adamantan-2-amine derivatives was proposed.

  DOI：

  10.1134/s1070363219080280
• 作为产物：
  描述：

  2-氨基金刚烷 在 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-adamantyl)-2-azidoacetamide
  参考文献：
  名称：

  Triazoloamides as potent γ-secretase modulators with reduced hERG liability

  摘要：

  Synthesis and SAR studies of novel aryl triazoles as gamma secretase modulators (GSMs) are presented in this communication. Starting from our aryl triazole leads, optimization studies were continued and the series progressed towards novel amides and lactams. Triazole 57 was identified as the most potent analog in this series, displaying single-digit nanomolar A beta 42 IC50 in cell-based assays and reduced affinity for the hERG channel. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.054