(2R,3S)-4-(adamant-1-ylamino)-2,3-methano-2-phenylbutan-1-ol | 473544-99-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3S)-4-(adamant-1-ylamino)-2,3-methano-2-phenylbutan-1-ol
• 英文别名: [(1R,2S)-2-[(1-adamantylamino)methyl]-1-phenylcyclopropyl]methanol
• CAS: 473544-99-9
• 化学式: C₂₁H₂₉NO
• 分子量: 311.467
• InChiKey: WFMBIDNZYJMBQN-PESGCIROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-4-(adamant-1-ylamino)-2,3-methano-2-phenylbutan-1-ol 、 碘甲烷 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以68%的产率得到(+)-(2R,3S)-4-(N-adamant-1-yl-N-methylamino)-2,3-methano-2-phenylbutan-1-ol
  参考文献：
  名称：

  Convenient synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist

  摘要：

  We have achieved a convenient enantioselective synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist in 19-40% overall chemical yields from the corresponding 2-arylbut-2-ene-1,4-diols with moderate to excellent asymmetric yields via regioselective acetylation using porcine pancreas lipase, catalytic enantioselective Simmons-Smith reactions, and amidation in aqueous organic solvent. This synthetic route is more efficient and less expensive than conventional methods. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.010
• 作为产物：
  描述：

  (1R,2S)-2-(Adamantan-1-ylaminomethyl)-1-phenyl-cyclopropanecarboxylic acid methyl ester 在 alane N,N-dimethylethylamine complex 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (2R,3S)-4-(adamant-1-ylamino)-2,3-methano-2-phenylbutan-1-ol
  参考文献：
  名称：

  Synthesis of (+)- and (−)-cis-2-[(1-adamantylamino)-methyl]-1-phenylcyclopropane derivatives as high affinity probes for σ1 and σ2 binding sites

  摘要：

  Selective ligands for either sigma(1) (sigma(1)) or sigma(2) binding sites are potentially useful for gaining a better understanding of the physiological functions of these proteins. Moreover, potent and selective homochiral sigma(1) and sigma(2) binding site ligands represent leads to potential radioligands for tumour imaging with positron emission tomography (PET). On the basis of their structural similarity to previous leads, new (+)- and (-)-cis-2-[(1-adamantylamino)-methyl]-1-phenylcyclopropane derivatives were synthesised and their binding affinities for sigma(1) and sigma(2) binding sites were determined. Each enantiomer showed high affinity for both sigma(1) and sigma(2) binding sites, but only (-)-cis-methyl-2-{[1-adamantyl(methyl)amino]methyl}-1-phenylcyclopropane-carboxylate, (-)-4, showed appreciable selectivity for binding to sigma(1) versus sigma(2) sites. The enantiomers of cis-(2-{[1-adamantyl(methyl)amino]methyl}-1-phenylcyclopropyl)methanol, 6, expressed the highest affinity for sigma(1) and sigma(2) binding sites. Ligands (-)-4, (+)-6 and (-)-6 might be rapidly labelled in their N-methyl groups by methylation of the N-desmethyl analogues with [C-11]iodomethane to provide prospective radioligands for PET. The N-desmethyl analogues, which are also high affinity ligands, were prepared and shown to undergo satisfactory methylation with iodomethane. (C) 2002 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01170-3