phenyl[N-[N-benzyloxycarbonylglycinyl]-1-aminophenylmethyl]phosphinic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl[N-[N-benzyloxycarbonylglycinyl]-1-aminophenylmethyl]phosphinic acid
• 英文别名: Phenyl-[phenyl-[[2-(phenylmethoxycarbonylamino)acetyl]amino]methyl]phosphinic acid；phenyl-[phenyl-[[2-(phenylmethoxycarbonylamino)acetyl]amino]methyl]phosphinic acid
• 化学式: C₂₃H₂₃N₂O₅P
• 分子量: 438.42
• InChiKey: ALNOXYOXAAEFHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄氧羰基甘氨酰胺 在 水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 phenyl[N-[N-benzyloxycarbonylglycinyl]-1-aminophenylmethyl]phosphinic acid
  参考文献：
  名称：

  Synthesis of Phosphinopeptides via the Mannich Ligation

  摘要：

  Phosphinopeptides are a class of unnatural peptides containing a tetrahedral phosphorus atom and have potential for use as enzyme inhibitors. A series of phosphinopeptides were synthesized via the Mannich-type reaction of aryldichlorophosphines, aldehydes, and N-protected amino amides or peptide amides and subsequent aminolysis with amino esters or peptide esters. The current method named the Mannich ligation is an efficient route to synthesis of phosphinopeptides through convergent condensation.

  DOI：

  10.1021/ol070360s

文献信息

• Synthesis of phosphinodepsipeptides via the pseudo-four-component condensation reaction
  作者：Fanhua Meng、Jiaxi Xu

  DOI：10.1016/j.tet.2013.04.032

  日期：2013.6

  Phosphinodepsipeptides are recognized as an important class of enzyme inhibitors as tetrahedrally structural transition-state analogues to natural peptides. A series of phosphinodepsipeptides was synthesized in satisfactory yields via pseudo-four-component condensation reaction of 2-(N-benzoxycarbonylamino)alkanamides/peptide amides, aldehydes, and aryldichlorophosphines, followed by alcoholysis with hydroxyl esters. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of Phosphinopeptides via the Mannich Ligation
  作者：Bonan Li、Shuzong Cai、Da-Ming Du、Jiaxi Xu

  DOI：10.1021/ol070360s

  日期：2007.6.1

  Phosphinopeptides are a class of unnatural peptides containing a tetrahedral phosphorus atom and have potential for use as enzyme inhibitors. A series of phosphinopeptides were synthesized via the Mannich-type reaction of aryldichlorophosphines, aldehydes, and N-protected amino amides or peptide amides and subsequent aminolysis with amino esters or peptide esters. The current method named the Mannich ligation is an efficient route to synthesis of phosphinopeptides through convergent condensation.