(5R,7S)-benzyl 7-methyl-2-oxo-1-(pyrazin-2-yl)-1,8-diazaspiro[4.5]dec-3-ene-8-carboxylate | 1426254-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (5R,7S)-benzyl 7-methyl-2-oxo-1-(pyrazin-2-yl)-1,8-diazaspiro[4.5]dec-3-ene-8-carboxylate
• 英文别名: benzyl (5R,7S)-7-methyl-2-oxo-1-pyrazin-2-yl-1,8-diazaspiro[4.5]dec-3-ene-8-carboxylate
• CAS: 1426254-48-9
• 化学式: C₂₁H₂₂N₄O₃
• 分子量: 378.431
• InChiKey: VCWCVXLPDMPMKU-HRAATJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,4R)-1-benzyl 4-methyl 4-azido-2-methylpiperidine-1,4-dicarboxylate 在 sodium tetrahydroborate 、 copper(l) iodide 、 sodium ethanolate 、 caesium carbonate 、 溶剂黄146 、 甲基磺酰氯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二甲基乙二胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 (5R,7S)-benzyl 7-methyl-2-oxo-1-(pyrazin-2-yl)-1,8-diazaspiro[4.5]dec-3-ene-8-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Spiropiperidines as BACE-1 Aspartyl Protease Inhibitors via Late Stage N-Arylation of a 1,8-Diazaspiro[4.5]dec-3-en-2-one Pharmacophore

  摘要：

  A stereoselective synthesis of spiropiperidine compounds, exemplified by compound 1, was developed, which was based upon the late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore. Previously, compound 1 was prepared in low overall yield from piperidinone 2 via the Strecker reaction. A new route was developed, which employed the stereospecific Corey-Link reaction of an enantiomerically pure trichloromethylcarbinol to give a template compound amenable to late stage N-arylation.

  DOI：

  10.1021/jo400016m

文献信息

• Stereoselective Synthesis of Spiropiperidines as BACE-1 Aspartyl Protease Inhibitors via Late Stage <i>N</i>-Arylation of a 1,8-Diazaspiro[4.5]dec-3-en-2-one Pharmacophore
  作者：Che-Wah Lee、Ricardo Lira、Jason Dutra、Kevin Ogilvie、Brian T. O’Neill、Michael Brodney、Christopher Helal、Joseph Young、Erik Lachapelle、Subas Sakya、John C. Murray

  DOI：10.1021/jo400016m

  日期：2013.3.15

  A stereoselective synthesis of spiropiperidine compounds, exemplified by compound 1, was developed, which was based upon the late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore. Previously, compound 1 was prepared in low overall yield from piperidinone 2 via the Strecker reaction. A new route was developed, which employed the stereospecific Corey-Link reaction of an enantiomerically pure trichloromethylcarbinol to give a template compound amenable to late stage N-arylation.