(4aS,9aS)-N-benzyl-11-(cyclopropylmethyl)-6-hydroxy-1,4-dihydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxamide | 1372868-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (4aS,9aS)-N-benzyl-11-(cyclopropylmethyl)-6-hydroxy-1,4-dihydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxamide
• CAS: 1372868-16-0
• 化学式: C₂₈H₃₂N₂O₂
• 分子量: 428.574
• InChiKey: GSIVVMWCXIZWND-IZLXSDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.57
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(4aS,9aS)-N-benzyl-11-(cyclopropylmethyl)-6-hydroxy-1,4-dihydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxamide
  参考文献：
  名称：

  Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology. Part 2: Propellane derivatives with an amide side chain

  摘要：

  We designed and synthesized propellane derivatives with a 6- or 7-amide side chain on the basis of the active conformation of the kappa selective agonist nalfurafine. The 6-amides showed high affinities for the kappa receptor, and one of the 6 beta-amides showed higher kappa selectivity than nalfurafine. On the other hand, although the affinities of the 7-amides decreased compared to the 6-amides, some 7 alpha-amides showed the highest selectivities for the kappa receptor among the tested compounds. The affinities of 7 beta-isomers were extremely low, which was postulated to result from the shielding effect of the 7 beta-amide side chain against the lone electron pair on the 17-nitrogen. This is the first conformational information about the 7-amide side chain in propellane derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.082