(E)-2,3-methano-5-bromopentan-1-ol | 129920-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2,3-methano-5-bromopentan-1-ol
• 英文别名: [(1R,2S)-2-(2-bromoethyl)cyclopropyl]methanol
• CAS: 129920-68-9
• 化学式: C₆H₁₁BrO
• 分子量: 179.057
• InChiKey: YWIUPHUHDBXHME-RITPCOANSA-N

物化性质

• 沸点：
  223.8±13.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-2,3-methano-5-bromopentan-1-ol 在 aluminum oxide 、 氯化铵 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成 (E)-2-amino-3,4-methano-6-(diethylphosphono)hexanenitrile
  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：

  重氮乙酸乙酯 、 4-溴-1-丁烯 在 lithium aluminium tetrahydride 、 copper(II) sulfate 作用下， 生成 (E)-2,3-methano-5-bromopentan-1-ol
  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