N-[3-(2-oxo-3-phenylmethoxypyridin-1-yl)propyl]prop-2-enamide | 1420812-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[3-(2-oxo-3-phenylmethoxypyridin-1-yl)propyl]prop-2-enamide
• CAS: 1420812-54-9
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: XDUICAPPZIMTBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-(2-oxo-3-phenylmethoxypyridin-1-yl)propyl]prop-2-enamide 在 氢溴酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

  摘要：

  The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10 were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.136
• 作为产物：
  描述：

  丙烯酰氯 、 3-[3-(benzyloxy)-2-oxopyridin-1(2H)-yl]propanamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到N-[3-(2-oxo-3-phenylmethoxypyridin-1-yl)propyl]prop-2-enamide
  参考文献：
  名称：

  3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

  摘要：

  The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10 were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.136

文献信息

• 3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators
  作者：Gloria Martinez、Jayanthi Arumugam、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tetlet.2012.11.136

  日期：2013.2

  The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10 were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates. (c) 2012 Elsevier Ltd. All rights reserved.