5-叠氮戊酰胺 | 1360453-32-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-叠氮戊酰胺
• 英文名称: 5-azidopentanamide
• 英文别名: 5-Azidopentanamide
• CAS: 1360453-32-2
• 化学式: C₅H₁₀N₄O
• 分子量: 142.161
• InChiKey: XAYNKHWMBDCGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-叠氮戊酰胺 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以84%的产率得到哌啶酮
  参考文献：
  名称：

  通过 Bu3SnH 介导的叠氮酰胺还原环化一锅法合成五元、六元和七元内酰胺

  摘要：

  我们的内酰胺化过程涉及使用三苯基膦和水来提供各种 γ- 和 δ- 内酰胺，产率从良好到极好。由于内酰胺在天然产物和药物中的重要性，开发了新的和多样化的高效、单步内酰胺途径具有扩展底物范围的叠氮基酰胺合成是非常可取的。因此，我们计划开发另一种方法用于各种叠氮基酰胺的直接内酰胺化，包括 1,5-叠氮基酰胺以制备 e-内酰胺。在这里，我们报告了通过 Bu 对 1,3-、1,4- 和 1,5-叠氮基酰胺进行单锅内酰胺化

  DOI：

  10.5012/bkcs.2012.33.2.739
• 作为产物：
  描述：

  5-叠氮基戊酸 在 ammonium hydroxide 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 5-叠氮戊酰胺
  参考文献：
  名称：

  Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach

  摘要：

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.

  DOI：

  10.1021/jacs.0c06877

文献信息

• One-Pot Synthesis of Five-, Six-, and Seven-Membered Lactams via Bu₃SnH-Mediated Reductive Cyclization of Azido Amides
  作者：Su-Jeong Lee、In-Jung Heo、Chang-Woo Cho

  DOI：10.5012/bkcs.2012.33.2.739

  日期：2012.2.20

  involves the use of triphenylphosphines and water toafford various γ- and δ-lactams in good to excellent yields.Owing to the importance of lactams in natural products andpharmaceuticals, the development of new and diverse routesfor efficient, single-step lactam synthesis from azido amideswith expanded substrate scope is highly desirable. There-fore, we planned to develop another methodology for thedirect

  我们的内酰胺化过程涉及使用三苯基膦和水来提供各种 γ- 和 δ- 内酰胺，产率从良好到极好。由于内酰胺在天然产物和药物中的重要性，开发了新的和多样化的高效、单步内酰胺途径具有扩展底物范围的叠氮基酰胺合成是非常可取的。因此，我们计划开发另一种方法用于各种叠氮基酰胺的直接内酰胺化，包括 1,5-叠氮基酰胺以制备 e-内酰胺。在这里，我们报告了通过 Bu 对 1,3-、1,4- 和 1,5-叠氮基酰胺进行单锅内酰胺化
• Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach
  作者：Jason S. Hoki、Henry H. Le、Karlie E. Mellott、Ying K. Zhang、Bennett W. Fox、Pedro R. Rodrigues、Yan Yu、Maximilian J. Helf、Joshua A. Baccile、Frank C. Schroeder

  DOI：10.1021/jacs.0c06877

  日期：2020.10.28

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.
• Direct Lactamization of Azido Amides via Staudinger-Type Reductive Cyclization
  作者：In-Jung Heo、Su-Jeong Lee、Chang-Woo Cho

  DOI：10.5012/bkcs.2012.33.1.333

  日期：2012.1.20