2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid | 952661-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid
• 英文别名: 2-Phenacyloxycarbonylpent-4-ynylphosphinic acid
• CAS: 952661-08-4
• 化学式: C₁₄H₁₅O₅P
• 分子量: 294.244
• InChiKey: IIHOHJWUICHXFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid 在 magnesium 、 溶剂黄146 、 三氟乙酸 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-({(1-adamantyloxy)[(5S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl]phosphoryl}methyl)-4-pentynoic acid
  参考文献：
  名称：

  A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics

  摘要：

  [GRAPHICS]The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochernistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

  DOI：

  10.1021/jo071081l
• 作为产物：
  描述：

  、 2-溴苯乙酮 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以55%的产率得到2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid
  参考文献：
  名称：

  A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics

  摘要：

  [GRAPHICS]The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochernistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

  DOI：

  10.1021/jo071081l