2-benzyl-3-oxo-(2-oxo-2-phenylethoxy)propyl{1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinyl}phosphinic acid | 952661-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-benzyl-3-oxo-(2-oxo-2-phenylethoxy)propyl{1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinyl}phosphinic acid
• 英文别名: (2-benzyl-3-oxo-3-phenacyloxypropyl)-[1-(9H-fluoren-9-ylmethoxycarbonyl)piperidin-2-yl]phosphinic acid
• CAS: 952661-17-5
• 化学式: C₃₈H₃₈NO₇P
• 分子量: 651.696
• InChiKey: CGWURSWFXLXIES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-oxo-(2-oxo-2-phenylethoxy)propyl{1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinyl}phosphinic acid 在 magnesium 、 溶剂黄146 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-((1-adamantyloxy){1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinyl}phosphoryl)-2-benzylpropanoic 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：

  9H-芴-9-基甲基(5-羟基戊基)氨基甲酸酯 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 乙酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 2-benzyl-3-oxo-(2-oxo-2-phenylethoxy)propyl{1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinyl}phosphinic 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

文献信息

• A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics
  作者：Magdalini Nasopoulou、Dimitris Georgiadis、Magdalini Matziari、Vincent Dive、Athanasios Yiotakis

  DOI：10.1021/jo071081l

  日期：2007.9.1

  [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.