(1R,6R)-8-acetyl-9-methyl-(3R-phenyl-5H-oxazolo[3,2-a])-2-aza-spiro[5.5]undec-8-ene

• 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: (1R,6R)-8-acetyl-9-methyl-(3R-phenyl-5H-oxazolo[3,2-a])-2-aza-spiro[5.5]undec-8-ene
• 英文别名: 1-[(3R,8S,8aR)-2'-methyl-3-phenylspiro[2,3,5,6,7,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-8,5'-cyclohexene]-1'-yl]ethanone
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: GQBGQBGJXKACMF-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 盐酸 、 镍 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 144.5h， 生成 (1R,6R)-8-acetyl-9-methyl-(3R-phenyl-5H-oxazolo[3,2-a])-2-aza-spiro[5.5]undec-8-ene
  参考文献：
  名称：

  New Piperidine Scaffolds via Nucleophilic Reactivity of (−)-Phenyloxazolopiperidine

  摘要：

  The present work illustrates the power of compound 2 as a chiral, nonracemic, and stable 2-piperideine (enamine) equivalent in the rapid and efficient construction of 3-substituted piperidines (carbon-carbon and carbon-sulfur bonds) such as 3-spiropiperidines. This methodology offers a new route to such systems that could compete with previously reported strategies.

  DOI：

  10.1021/jo0499524

文献信息

• New Piperidine Scaffolds via Nucleophilic Reactivity of (−)-Phenyloxazolopiperidine
  作者：Erwan Poupon、David François、Nicole Kunesch、Henri-Philippe Husson

  DOI：10.1021/jo0499524

  日期：2004.5.1

  The present work illustrates the power of compound 2 as a chiral, nonracemic, and stable 2-piperideine (enamine) equivalent in the rapid and efficient construction of 3-substituted piperidines (carbon-carbon and carbon-sulfur bonds) such as 3-spiropiperidines. This methodology offers a new route to such systems that could compete with previously reported strategies.