(S)-6-bromospiro[chroman-2,1'-cyclobutan]-4-amine | 1373320-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-6-bromospiro[chroman-2,1'-cyclobutan]-4-amine
• 英文别名: (4S)-6-bromospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-amine
• CAS: 1373320-34-3
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: PKUAXIJJZUGPIS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-bromospiro[chroman-2,1'-cyclobutan]-4-amine 在 四(三苯基膦)钯 、 lithium perchlorate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 40.0h， 生成 (2R,3S)-3-amino-1-((S)-6-neopentylspiro[chroman-2,1'-cyclobutane]-4-ylamino)-4-phenylbutan-2-ol
  参考文献：
  名称：

  A Potent and Orally Efficacious, Hydroxyethylamine-Based Inhibitor of β-Secretase

  摘要：

  beta-Secretase inhibitors are potentially disease-modifying treatments for Alzheimer's disease. Previous efforts in our laboratory have resulted in hydroxyethylamine-derived inhibitors such as 1 with low nanomolar potency against beta-site amyloid precursor protein cleaving enzyme (BACE). When dosed intravenously, compound 1 was also shown to significantly reduce A beta(40) levels in plasma, brain, and cerebral spinal fluid. Herein, we report further optimizations that led to the discovery of inhibitor 16 as a novel, potent, and orally efficacious BACE inhibitor.

  DOI：

  10.1021/ml3000148