(+)-(7S,10S)-5-benzyl-10-phenyl-9-oxa-1,5-diazabicyclo[5.3.0]decane-2,6-dione | 1145667-66-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(7S,10S)-5-benzyl-10-phenyl-9-oxa-1,5-diazabicyclo[5.3.0]decane-2,6-dione
• 英文别名: (3S,9aS)-8-benzyl-3-phenyl-3,6,7,9a-tetrahydro-1H-[1,3]oxazolo[3,4-a][1,4]diazepine-5,9-dione
• CAS: 1145667-66-8
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: SRJGYNHSEVQFQE-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 苄胺 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以25%的产率得到(-)-(7S,10R)-5-benzyl-10-phenyl-9-oxa-1,5-diazabicyclo[5.3.0]decane-2,6-dione
  参考文献：
  名称：

  1,4-Diazepanes derived from (S)-serine – Homopiperazines with improved σ1 (sigma) receptor affinity and selectivity

  摘要：

  Starting from the proteinogenic amino acid (S)-serine chiral non-racemic 1,4-diazepanes 4 with a hydroxymethyl residue in position 2 are synthesized and pharmacologically evaluated. The key step in the synthesis is the formation of the bicyclic system 8 by consecutive nucleophilic substitution of the chloropropionamide 7 with primary amines and intramolecular aminolysis. Both reaction steps require catalysis with the Lewis acid Ti(O-iPr)(4). Homologation of the piperazine to the 1,4-diazepane ring results in a remarkable improvement of sigma(1) receptor affinity and sigma(1)/sigma(2) selectivity. The 1,4-dibenzyl derivative 4a interacts with a K-i value of 7.4 nM with sigma(1) receptors and shows a 53-fold selectivity for sigma(1) receptors over sigma(2) receptors. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.033