6'-fluoro-1'-methylspiro[azetidine-3,4'-benzo[d][1,3]oxazin]-2'(1'H)-one | 1563182-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6'-fluoro-1'-methylspiro[azetidine-3,4'-benzo[d][1,3]oxazin]-2'(1'H)-one
• 英文别名: 6-fluoro-1-methylspiro[3,1-benzoxazine-4,3'-azetidine]-2-one
• CAS: 1563182-62-6
• 化学式: C₁₁H₁₁FN₂O₂
• 分子量: 222.219
• InChiKey: UMLDJHWSCLSJLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6'-fluoro-1'-methylspiro[azetidine-3,4'-benzo[d][1,3]oxazin]-2'(1'H)-one 、 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以84%的产率得到2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y
• 作为产物：
  描述：

  tert-butyl 6'-fluoro-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-carboxylate 在 盐酸 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 6'-fluoro-1'-methylspiro[azetidine-3,4'-benzo[d][1,3]oxazin]-2'(1'H)-one
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y