3-(3-methyl-2-butylideneaminoxy)-1-isopropylamino-2-propanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(3-methyl-2-butylideneaminoxy)-1-isopropylamino-2-propanol
• 英文别名: 1-[(E)-3-methylbutan-2-ylideneamino]oxy-3-(propan-2-ylamino)propan-2-ol
• 化学式: C₁₁H₂₄N₂O₂
• 分子量: 216.324
• InChiKey: DRHXBGOZLPWFEA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  53.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methyl-butan-2-one oxime 在 1.) MaONa 作用下， 以 乙醇 为溶剂， 反应 145.0h， 生成 3-(3-methyl-2-butylideneaminoxy)-1-isopropylamino-2-propanol
  参考文献：
  名称：

  Conformationally restrained β-blocking oxime ethers: synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-isoxazolidinyl)-ethanolamines

  摘要：

  The diastereoisomeric N-isopropyl- and N-t-butyl-substituted 2-(5'-(3'-phenyl)- and 2-(5'-(3'-isopropyl)isoxazolidinyl)-ethanolamines (5-8), which can be viewed as conformationally restrained analogs of the corresponding beta-blocking oxime ethers 10 and 11, were synthesized. The relative configurations of 5-8 were assigned by H-1-NMR studies and by the determination of the solid state structure of one of the new compounds (6a). The new isoxazoline derivatives (5-8) were tested both by radioligand binding assays and by functional tests on isolated preparations. Compounds 5a-8a were found to retain, albeit to a lower extent, the beta-blocking properties of the corresponding oxime ethers 10a and 11a, thus indicating that these last compounds may prove to be still capable of interacting with the beta-receptors, even if their C = NOCH2 portion is constrained in a conformationally semi-rigid isoxazoline structure. Possible rationalizations of the results were sought by comparing the conformations and the molecular reactivity of model compounds of the isoxazolines 5-8 and of the oxime ethers 10 and 11.

  DOI：

  10.1016/0223-5234(92)90110-m

文献信息

• Conformationally restrained β-blocking oxime ethers: synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-isoxazolidinyl)-ethanolamines
  作者：A Balsamo、MC Breschi、M Chini、P Domiano、G Giannaccini、A Lucacchini、B Macchia、M Macchia、C Manera、A Martinelli、C Martini、E Martinotti、P Nieri、A Rossello

  DOI：10.1016/0223-5234(92)90110-m

  日期：1992.11

  The diastereoisomeric N-isopropyl- and N-t-butyl-substituted 2-(5'-(3'-phenyl)- and 2-(5'-(3'-isopropyl)isoxazolidinyl)-ethanolamines (5-8), which can be viewed as conformationally restrained analogs of the corresponding beta-blocking oxime ethers 10 and 11, were synthesized. The relative configurations of 5-8 were assigned by H-1-NMR studies and by the determination of the solid state structure of one of the new compounds (6a). The new isoxazoline derivatives (5-8) were tested both by radioligand binding assays and by functional tests on isolated preparations. Compounds 5a-8a were found to retain, albeit to a lower extent, the beta-blocking properties of the corresponding oxime ethers 10a and 11a, thus indicating that these last compounds may prove to be still capable of interacting with the beta-receptors, even if their C = NOCH2 portion is constrained in a conformationally semi-rigid isoxazoline structure. Possible rationalizations of the results were sought by comparing the conformations and the molecular reactivity of model compounds of the isoxazolines 5-8 and of the oxime ethers 10 and 11.