methyl (2S,4aR,9aR)-11-(cyclopropylmethyl)-6-methoxy-3-oxo-1,2,3,4-tetrahydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxylate | 1372867-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl (2S,4aR,9aR)-11-(cyclopropylmethyl)-6-methoxy-3-oxo-1,2,3,4-tetrahydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxylate
• CAS: 1372867-72-5
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: HUSQXXIPQGWDDC-CDNPAEQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,4aR,9aR)-11-(cyclopropylmethyl)-6-methoxy-3-oxo-1,2,3,4-tetrahydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxylate 在 sodium tetrahydroborate 、 正丁基锂 、 palladium on activated charcoal 、 氢气 、 三溴化硼 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  (1R,9R)-11-(cyclopropylmethyl)-4-methoxy-11-azatetracyclo[7.4.4.01,9.02,7]heptadeca-2(7),3,5-trien-15-one 、 碳酸二甲酯 在 sodium hydride 作用下， 生成 methyl (2S,4aR,9aR)-11-(cyclopropylmethyl)-6-methoxy-3-oxo-1,2,3,4-tetrahydro-9H-4a,9a-(ethanoiminomethano)fluorene-2-carboxylate 、
  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