(S)-6-neopentylspiro[chroman-2,1'-cyclobutan]-4-amine | 1373320-35-4

• 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-neopentylspiro[chroman-2,1'-cyclobutan]-4-amine
• 英文别名: (4S)-6-(2,2-dimethylpropyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-amine
• CAS: 1373320-35-4
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: OONFNHOGKOXVJN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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-neopentylspiro[chroman-2,1'-cyclobutan]-4-amine 在 lithium perchlorate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 C₂₉H₄₀N₂O₃
  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
• 作为产物：
  描述：

  (S)-6-bromospiro[chroman-2,1'-cyclobutan]-4-amine 、 (1s,5s)-9-neopentyl-9-bora-bicyclo[3.3.1]nonane 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (S)-6-neopentylspiro[chroman-2,1'-cyclobutan]-4-amine
  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