(3S)-3-tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydropyridine N-oxide | 1395819-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3S)-3-tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydropyridine N-oxide
• 英文别名: tert-butyl-[[(5S)-1-oxido-2,3,4,5-tetrahydropyridin-1-ium-5-yl]oxy]-diphenylsilane
• CAS: 1395819-03-0
• 化学式: C₂₁H₂₇NO₂Si
• 分子量: 353.536
• InChiKey: WYBRIOSJMVPXOX-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydropyridine N-oxide 在 indium 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 5.0h， 生成 (2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylpiperidine
  参考文献：
  名称：

  A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton

  摘要：

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.

  DOI：

  10.1021/jo3011914
• 作为产物：
  描述：

  (2S)-2-(tert-butyldiphenylsilyloxy)pentane-1,5-diol 在 manganese(IV) oxide 、 盐酸羟胺 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (3S)-3-tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydropyridine N-oxide 、 (5S)-5-tert-butyldiphenylsilyloxy-3,4,5,6-tetrahydropyridine N-oxide
  参考文献：
  名称：

  A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton

  摘要：

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.

  DOI：

  10.1021/jo3011914

文献信息

• A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton
  作者：Glenn Archibald、Chih-Pei Lin、Peter Boyd、David Barker、Vittorio Caprio

  DOI：10.1021/jo3011914

  日期：2012.9.21

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.