benzyl 2,4-dibromo-3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate | 1542468-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: benzyl 2,4-dibromo-3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate
• CAS: 1542468-56-3
• 化学式: C₁₅H₁₃Br₂NO₃
• 分子量: 415.081
• InChiKey: VIWMKFHPAUNEOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,4-dibromo-3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate 在 甲酸 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 、 氯化铵 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (+/-)-exo-6-(6-fluoro-pyridin-3-yl)-3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of both enantiomers of [18F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors

  摘要：

  Both enantiomers of the epibatidine analogue flubatine display high affinity towards the alpha 4 beta 2 nicotinic acetylcholine receptor (nAChR) in vitro, accompanied by negligible interactions with diverse off-target proteins. Extended single dose toxicity studies in rodent indicated a NOEL (No Observed Effect Level) of 6.2 mu g/kg for (-)-flubatine and 1.55 mu g/kg for (+)-flubatine. We developed syntheses for both flubatine enantiomers and their corresponding precursors for radiolabeling. The newly synthesized trimethylammonium precursors allowed for highly efficient F-18-radiolabelling in radiochemical yields >60% and specific activities >750 GBq/mu mol, thus making the radioligands practical for clinical investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.011
• 作为产物：
  描述：

  1,1,3,3-四溴丙酮 、 benzyl 1H-pyrrole-1-carboxylate 在 diethylzinc 作用下， 以 甲苯 为溶剂， 生成 benzyl 2,4-dibromo-3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of both enantiomers of [18F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors

  摘要：

  Both enantiomers of the epibatidine analogue flubatine display high affinity towards the alpha 4 beta 2 nicotinic acetylcholine receptor (nAChR) in vitro, accompanied by negligible interactions with diverse off-target proteins. Extended single dose toxicity studies in rodent indicated a NOEL (No Observed Effect Level) of 6.2 mu g/kg for (-)-flubatine and 1.55 mu g/kg for (+)-flubatine. We developed syntheses for both flubatine enantiomers and their corresponding precursors for radiolabeling. The newly synthesized trimethylammonium precursors allowed for highly efficient F-18-radiolabelling in radiochemical yields >60% and specific activities >750 GBq/mu mol, thus making the radioligands practical for clinical investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.011