(R)-6-Allyl-11-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; hydrochloride | 130794-70-6

• 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: (R)-6-Allyl-11-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; hydrochloride
• 英文别名: (6aR)-11-methoxy-6-prop-2-enyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;hydrochloride
• CAS: 130794-70-6
• 化学式: C₂₀H₂₁NO*ClH
• 分子量: 327.854
• InChiKey: HLMSVNNEJICLIT-UNTBIKODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-6-Allyl-11-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; hydrochloride 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到11-羟基-N-烯丙基去甲阿朴啡
  参考文献：
  名称：

  (R)- and (S)-enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue

  摘要：

  The R-(-)- and S-(+)-enantiomers of 11-hydroxy-N-allyl (4), and 10,11-dihydroxy-N-allyl (3) congeners of 11-hydroxy-N-n-propylnoraporphine (11-OH-NPa, 2) or N-n-propylnorapomorphine (NPA, 1) were synthesized. Binding affinity of these compounds at dopamine (DA) receptor sites was evaluated with a membrane preparation of corpus striatum from rat brain. The R/S enantiomeric receptor affinity ratio was enhanced by allylic substitution of 3 and 4 and their R isomers had high DA receptor affinity similar to that of the N-n-propyl congeners. These N-allylaporphines are proposed as useful precursors to the preparation of their tritiated N-n-propyl enantiomers.

  DOI：

  10.1021/jm00105a005
• 作为产物：
  描述：

  (6aR)-11-methoxy-6-prop-2-enyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;(2R,3R)-2,3-dibenzoyloxybutanedioic acid 、 盐酸 生成 (R)-6-Allyl-11-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; hydrochloride
  参考文献：
  名称：

  NEUMEYER, JOHN L.;GAO, YIGONG;KULA, NORA S.;BALDESSARINI, ROSS J., J. MED. CHEM., 34,(1991) N, C. 24-28

  摘要：

  DOI：