(S)-1-[(S)-5-(4-Chloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethane-1,2-diol | 177950-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-[(S)-5-(4-Chloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethane-1,2-diol
• 英文别名: (1S)-1-[(5S)-5-(4-chlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]ethane-1,2-diol
• CAS: 177950-47-9
• 化学式: C₁₁H₁₂ClNO₃
• 分子量: 241.674
• InChiKey: AWBTXRZVALSFDO-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-[(S)-5-(4-Chloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethane-1,2-diol 在 吡啶 、 sodium 、 对甲苯磺酰氯 作用下， 以 乙醇 、 苯 为溶剂， 反应 89.0h， 生成 (R)-2-tert-Butylamino-1-[(S)-5-(4-chloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethanol
  参考文献：
  名称：

  Chiral 2-(3′-(5′-p-chlorophenyl)isoxazolidinyl)ethanolamines as conformationally restrained analogs of methyloxyiminomethyl (MOIM) β-adrenergic antagonists: synthesis, configuration and β-adrenergic properties

  摘要：

  The chiral N-isopropyl- and N-t-butyl-substituted 2-(3'-(5'-p-chlorophenyl)isoxazolidinyl) ethanolamines 2, 3, which can be viewed as conformationally restrained analogs of the corresponding methyloxyiminomethyl (MOIM) beta-adrenergic antagonists 1, were synthesized from optically active precursors with a known absolute configuration. The structure and configuration of the intermediate and final products 2, 3 were assigned on the basis of a comparison of the H-1-NMR spectral data of all compounds, crystallographic analysis of one of the intermediates [(2R,5'S)-7] and knowledge of the configuration of the chiral starting compounds 4. The new isoxazoline derivatives 2, 3 were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing affinity indices lower than 10 mu M on beta(1)-adrenoceptors were also assayed for their P-adrenergic activity by functional tests on isolated preparations. The results showed that the cyclic derivatives 2, 3 possess a capacity to interact with beta-receptors which is clearly lower than that of the corresponding MOIM analogs 1.

  DOI：

  10.1016/0223-5234(96)80366-7
• 作为产物：
  描述：

  (S)-5-(4-Chloro-phenyl)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydro-isoxazole 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以62%的产率得到(S)-1-[(S)-5-(4-Chloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethane-1,2-diol
  参考文献：
  名称：

  Chiral 2-(3′-(5′-p-chlorophenyl)isoxazolidinyl)ethanolamines as conformationally restrained analogs of methyloxyiminomethyl (MOIM) β-adrenergic antagonists: synthesis, configuration and β-adrenergic properties

  摘要：

  The chiral N-isopropyl- and N-t-butyl-substituted 2-(3'-(5'-p-chlorophenyl)isoxazolidinyl) ethanolamines 2, 3, which can be viewed as conformationally restrained analogs of the corresponding methyloxyiminomethyl (MOIM) beta-adrenergic antagonists 1, were synthesized from optically active precursors with a known absolute configuration. The structure and configuration of the intermediate and final products 2, 3 were assigned on the basis of a comparison of the H-1-NMR spectral data of all compounds, crystallographic analysis of one of the intermediates [(2R,5'S)-7] and knowledge of the configuration of the chiral starting compounds 4. The new isoxazoline derivatives 2, 3 were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing affinity indices lower than 10 mu M on beta(1)-adrenoceptors were also assayed for their P-adrenergic activity by functional tests on isolated preparations. The results showed that the cyclic derivatives 2, 3 possess a capacity to interact with beta-receptors which is clearly lower than that of the corresponding MOIM analogs 1.

  DOI：

  10.1016/0223-5234(96)80366-7

文献信息

• Chiral 2-(3′-(5′-p-chlorophenyl)isoxazolidinyl)ethanolamines as conformationally restrained analogs of methyloxyiminomethyl (MOIM) β-adrenergic antagonists: synthesis, configuration and β-adrenergic properties
  作者：A Balsamo、MC Breschi、G Chiellini、P Cozzini、P Domiano、M Macchia、C Manera、A Martinelli、S Nencetti、A Rossello、P Saccà、R Scatizzi

  DOI：10.1016/0223-5234(96)80366-7

  日期：1996.1

  The chiral N-isopropyl- and N-t-butyl-substituted 2-(3'-(5'-p-chlorophenyl)isoxazolidinyl) ethanolamines 2, 3, which can be viewed as conformationally restrained analogs of the corresponding methyloxyiminomethyl (MOIM) beta-adrenergic antagonists 1, were synthesized from optically active precursors with a known absolute configuration. The structure and configuration of the intermediate and final products 2, 3 were assigned on the basis of a comparison of the H-1-NMR spectral data of all compounds, crystallographic analysis of one of the intermediates [(2R,5'S)-7] and knowledge of the configuration of the chiral starting compounds 4. The new isoxazoline derivatives 2, 3 were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing affinity indices lower than 10 mu M on beta(1)-adrenoceptors were also assayed for their P-adrenergic activity by functional tests on isolated preparations. The results showed that the cyclic derivatives 2, 3 possess a capacity to interact with beta-receptors which is clearly lower than that of the corresponding MOIM analogs 1.