(E,S)-N-(2,3-epoxypropylidene)(p-chlorophenylmethyloxy)amine | 176200-55-8

• 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: (E,S)-N-(2,3-epoxypropylidene)(p-chlorophenylmethyloxy)amine
• 英文别名: (E)-N-[(4-chlorophenyl)methoxy]-1-[(2S)-oxiran-2-yl]methanimine
• CAS: 176200-55-8
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: LJTQQVSQLRGDPE-YIVIPITNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 (E,S)-N-(2,3-epoxypropylidene)(p-chlorophenylmethyloxy)amine 以 乙醇 、 苯 为溶剂， 反应 144.0h， 生成 (E,R)-N-[3-(tert-butylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amine
  参考文献：
  名称：

  New chiral methyloxyiminomethyl (MOIM) β-adrenergic antagonists. (S)- and (R)-N-[3-(alkylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines as probes for determining enantiomeric specificity in the class of MOIM-type β-adrenergic blocking agents

  摘要：

  The chiral (S)- and (R)-N-[3-(isopropylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines ((S)-1a and (R)-1a) and their corresponding N-tert-butyl-substituted analogs ((S)-1b and (R)-1b) were synthesized from optically active precursors of known absolute configuration by procedures which had no effect on the configuration of the asymmetric carbon. Compounds (S)-1a,b and (R)-1a,b were tested for their beta-adrenergic properties by radioligand binding experiments and functional tests on isolated preparations. The biopharmacological results show that compounds (S)-1a,b, in which the geometry of the chiral carbon adjacent to the hydroxyl group resembles that of natural catecholamines with the R configuration, interacted better with beta-receptors, even if the stereochemical selectivity among enantiomeric pairs is not particularly marked.

  DOI：

  10.1016/0223-5234(96)89135-5
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-3-(4-chloro-benzyloxyimino)-2-hydroxy-propyl ester 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 生成 (E,S)-N-(2,3-epoxypropylidene)(p-chlorophenylmethyloxy)amine
  参考文献：
  名称：

  New chiral methyloxyiminomethyl (MOIM) β-adrenergic antagonists. (S)- and (R)-N-[3-(alkylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines as probes for determining enantiomeric specificity in the class of MOIM-type β-adrenergic blocking agents

  摘要：

  The chiral (S)- and (R)-N-[3-(isopropylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines ((S)-1a and (R)-1a) and their corresponding N-tert-butyl-substituted analogs ((S)-1b and (R)-1b) were synthesized from optically active precursors of known absolute configuration by procedures which had no effect on the configuration of the asymmetric carbon. Compounds (S)-1a,b and (R)-1a,b were tested for their beta-adrenergic properties by radioligand binding experiments and functional tests on isolated preparations. The biopharmacological results show that compounds (S)-1a,b, in which the geometry of the chiral carbon adjacent to the hydroxyl group resembles that of natural catecholamines with the R configuration, interacted better with beta-receptors, even if the stereochemical selectivity among enantiomeric pairs is not particularly marked.

  DOI：

  10.1016/0223-5234(96)89135-5