(R)-N-benzylnorapocodeine hydrochloride | 130699-48-8

• 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)-N-benzylnorapocodeine hydrochloride
• 英文别名: (6aR)-6-benzyl-10-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol;hydrochloride
• CAS: 130699-48-8
• 化学式: C₂₄H₂₃NO₂*ClH
• 分子量: 393.913
• InChiKey: WEIJVHLEVSPJBI-VEIFNGETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-benzylnorapocodeine hydrochloride 在 palladium on activated charcoal 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 81.0h， 生成 (RS)-(+/-)-10,11-dimethoxynoraporphine hydrochloride
  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：

  (4R,7S,7aR,12bS)-3-benzyl-9-methoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;methanesulfonic acid 生成 (R)-N-benzylnorapocodeine 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：