diisopropyl 1,1-difluoro-2-N-phthalimidoethane-1-phosphonate | 160485-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diisopropyl 1,1-difluoro-2-N-phthalimidoethane-1-phosphonate
• CAS: 160485-80-3
• 化学式: C₁₆H₂₀F₂NO₅P
• 分子量: 375.309
• InChiKey: MZYGFQRVRRHFID-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±45.0 °C(predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diisopropyl 1,1-difluoro-2-N-phthalimidoethane-1-phosphonate 在 对甲苯磺酸 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 tetraisopropyl 1,1,5,5-tetrafluoro-2-oxo-3-azapentane-1,5-bisphosphonate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y
• 作为产物：
  描述：

  N-溴甲基邻苯二甲酰亚胺 、 diisopropyl (bromodifluoromethyl)phosphonate 在 copper(I) bromide 、 锌 作用下， 反应 3.0h， 以50%的产率得到diisopropyl 1,1-difluoro-2-N-phthalimidoethane-1-phosphonate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y