(E)-2,3-methano-4-(diethylphosphono)butanal | 129920-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (E)-2,3-methano-4-(diethylphosphono)butanal
• CAS: 129920-54-3
• 化学式: C₉H₁₇O₄P
• 分子量: 220.205
• InChiKey: GWLJMOVAIMZRFJ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-2,3-methano-4-(diethylphosphono)butanal 在 盐酸 、 aluminum oxide 、 氯化铵 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 (E)-2-amino-3,4-methano-5-phosphonopentanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid

  摘要：

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).

  DOI：

  10.1021/jm00105a024
• 作为产物：
  描述：

  2,3-methano-4-(diethylphosphono)butanoic acid 在 硼烷四氢呋喃络合物 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-2,3-methano-4-(diethylphosphono)butanal
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid

  摘要：

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).

  DOI：

  10.1021/jm00105a024