((S)-1-Phenyl-ethyl)-carbamic acid (S)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl ester | 114033-67-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: ((S)-1-Phenyl-ethyl)-carbamic acid (S)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl ester
• CAS: 114033-67-9
• 化学式: C₂₈H₃₀N₂O₂
• 分子量: 426.558
• InChiKey: ZFMNPRCAQRRWKF-CYFREDJKSA-N

物化性质

• 沸点：
  575.9±50.0 °C(predicted)
• 密度：
  1.161±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-(+)-11-methoxy-N-n-propylnoraporphine hydrochloride 在 氢溴酸 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 ((S)-1-Phenyl-ethyl)-carbamic acid (S)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl ester
  参考文献：
  名称：

  Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine

  摘要：

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.

  DOI：

  10.1021/jm00402a024