(Z)-2,3-methano-5-bromopentanal | 129920-71-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (Z)-2,3-methano-5-bromopentanal
• 英文别名: (1S,2S)-2-(2-bromoethyl)cyclopropane-1-carbaldehyde
• CAS: 129920-71-4
• 化学式: C₆H₉BrO
• 分子量: 177.041
• InChiKey: GLLZNRJKKFHEMR-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-methano-5-bromopentanal 在 盐酸 、 aluminum oxide 、 氯化铵 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 2-amino-2-(2-(2-phosphonoethyl)cyclopropyl)acetic 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：

  (Z)-ethyl 2,3-methano-5-bromopentanoate 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 (Z)-2,3-methano-5-bromopentanal
  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