norcodeine | 10118-79-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: norcodeine
• 英文别名: (4R,4aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• CAS: 10118-79-3
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: HKOIXWVRNLGFOR-JGYCMRFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  norcodeine 、 氯化苄 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 N-benzylnorcodeine
  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

文献信息

• (R)- and (S)-enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue
  作者：John L. Neumeyer、Nora S. Kula、Ross J. Baldessarini、Yigong Gao

  DOI：10.1021/jm00105a005

  日期：1991.1

  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.