(9S)-elaeocarpenine | 1220796-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (9S)-elaeocarpenine
• 英文别名: (S)-(1,2,3,5,6,8a-hexahydroindolizin-8-yl)(2-hydroxy-6-methylphenyl)methanone；[(8aS)-1,2,3,5,6,8a-hexahydroindolizin-8-yl]-(2-hydroxy-6-methylphenyl)methanone
• CAS: 1220796-53-1
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: KNSLYJICIDVPEX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (9S)-elaeocarpenine
  参考文献：
  名称：

  Synthesis and evaluation of opioid receptor-binding affinity of elaeocarpenine and its analogs

  摘要：

  Both enantiomers of elaeocarpenine (1) and its analogs, 21, 22, 25, and 27, were synthesized from bicyclic aldehydes 8-10 via a flexible route previously established for total synthesis of grandisines, and their binding affinities for mu-, kappa- and delta-opioid receptor subtypes were evaluated. We found that (9R)-1 exhibited higher affinity than (9S)-1 for all the subtypes, but the enantiomers showed little subtype selectivity. Analogs 21 having a pyrrolizidine skeleton and 27 having a stemona-type skeleton in place of the indolizidine unit of (9S)-1 showed mu-selective and mu-, kappa-selective binding, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.062