7-endo-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylic acid | 1443663-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 7-endo-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylic acid
• CAS: 1443663-93-1
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: IHFGMUIRMCCXCJ-JGPRNRPPSA-N

物化性质

• 沸点：
  400.9±38.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-endo-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Novel nicotinic acetylcholine receptor agonists containing carbonyl moiety as a hydrogen bond acceptor

  摘要：

  A novel series of alpha 4 beta 2 nAChR agonists lacking common pyridine or its bioisosteric heterocycle have been disclosed. Essential pharmacophoric elements of the series are exocyclic carbonyl moiety as a hydrogen bond acceptor and secondary amino group within diaza- or azabicyclic scaffold. Computer modeling studies suggested that molecular shape of the ligand also contributes to promotion of agonism. Proof of concept for improving working memory performance in a novel object recognition task has been demonstrated on a representative of the series, 3-propionyl-3,7-diazabicyclo[3.3.0]octane (34). (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.058
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 在 四氢吡咯 、 三乙胺 、 对甲苯磺酰肼 、 lithium hydroxide 作用下， 生成 7-endo-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylic acid
  参考文献：
  名称：

  Novel nicotinic acetylcholine receptor agonists containing carbonyl moiety as a hydrogen bond acceptor

  摘要：

  A novel series of alpha 4 beta 2 nAChR agonists lacking common pyridine or its bioisosteric heterocycle have been disclosed. Essential pharmacophoric elements of the series are exocyclic carbonyl moiety as a hydrogen bond acceptor and secondary amino group within diaza- or azabicyclic scaffold. Computer modeling studies suggested that molecular shape of the ligand also contributes to promotion of agonism. Proof of concept for improving working memory performance in a novel object recognition task has been demonstrated on a representative of the series, 3-propionyl-3,7-diazabicyclo[3.3.0]octane (34). (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.058

文献信息

• An Expedient and Practical Approach to Functionalized 3-Aza-, 3-Oxa-, and 3-Thiabicyclo[3.3.1]nonane Systems
  作者：Igor Komarov、Aleksandr Ishchenko、Stanislav Yanik、Eduard Rusanov、Anthony Kirby

  DOI：10.1055/s-0034-1379456

  日期：——

  Abstract The synthesis of a number of heterobicyclo[3.3.1]nonane derivatives possessing carbonyl, amino, or carboxyl groups is reported. The synthetic scheme is concise and practical, based on optimized reaction conditions for each step and an orthogonal protection group strategy. Procedures for the key synthetic steps (double annulation of α-bromomethyl acrylates to enamines and a Caglioti reaction)

  摘要 报道了许多具有羰基，氨基或羧基的杂双环[3.3.1]壬烷衍生物的合成。基于每个步骤的最佳反应条件和正交保护基策略，该合成方案简洁实用。关键合成步骤（丙烯酸α-溴甲基丙烯酸酯的双环化和烯胺反应和Caglioti反应）的程序得到了显着改善。这使得该化合物对药物化学具有吸引力，因为潜在的化学多样性3D支架可用于药物设计。 报道了许多具有羰基，氨基或羧基的杂双环[3.3.1]壬烷衍生物的合成。基于每个步骤的最佳反应条件和正交保护基策略，该合成方案简洁实用。关键合成步骤（丙烯酸α-溴甲基丙烯酸酯的双环化和烯胺反应和Caglioti反应）的程序得到了显着改善。这使得该化合物对药物化学具有吸引力，因为潜在的化学多样性3D支架可用于药物设计。