1-(2-溴乙基)-吡咯烷盐酸 | 90246-16-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 中文名称: 1-(2-溴乙基)-吡咯烷盐酸
• 英文名称: 8β--6,7-didehydro-4,5α-epoxy-3-hydroxy-17-methylmorphinan
• 英文别名: 8beta-(Bis(2-chloroethyl)amino)-6,7-didehydro-3-hydroxy-17-methyl-4,5alpha-epoxymorphinan；(4R,4aR,5S,7aS,12bS)-5-[bis(2-chloroethyl)amino]-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
• CAS: 90246-16-5
• 化学式: C₂₁H₂₆Cl₂N₂O₂
• 分子量: 409.356
• InChiKey: GDCFYXHPIMXXNG-XSLRHLANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  可待因 在 氯化亚砜 、 三溴化硼 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 18.0h， 生成 1-(2-溴乙基)-吡咯烷盐酸
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of an 8.beta.-bis(2-chloroethyl)amino opiate as a nonequilibrium opioid receptor probe

  摘要：

  8 beta-[Bis(2-chloroethyl)amino]-6,7-didehydro-3-hydroxy-17-methyl-4 ,5 alpha-epoxymorphinan (3) was synthesized from codeine, and its configuration at C-8 was determined by NMR. When evaluated in the guinea pig ileum and mouse vas deferens preparations, 3 was found to be a feeble, reversible agonist in both tissues without any irreversible agonist or antagonist activity. The fact that the 8 beta-bis-(2-hydroxyethyl)amino analogue was devoid of opioid activity suggests that steric hindrance to ligand-receptor association by a bulky 8-substituent may be responsible for this inactivity.

  DOI：

  10.1021/jm00374a026

文献信息

• Synthesis and pharmacological evaluation of an 8.beta.-bis(2-chloroethyl)amino opiate as a nonequilibrium opioid receptor probe
  作者：Sunan Fang、K. H. Bell、P. S. Portoghese

  DOI：10.1021/jm00374a026

  日期：1984.8

  8 beta-[Bis(2-chloroethyl)amino]-6,7-didehydro-3-hydroxy-17-methyl-4 ,5 alpha-epoxymorphinan (3) was synthesized from codeine, and its configuration at C-8 was determined by NMR. When evaluated in the guinea pig ileum and mouse vas deferens preparations, 3 was found to be a feeble, reversible agonist in both tissues without any irreversible agonist or antagonist activity. The fact that the 8 beta-bis-(2-hydroxyethyl)amino analogue was devoid of opioid activity suggests that steric hindrance to ligand-receptor association by a bulky 8-substituent may be responsible for this inactivity.