(6S)-6-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]piperidin-2-one | 1296689-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (6S)-6-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]piperidin-2-one
• CAS: 1296689-94-5
• 化学式: C₁₈H₂₉NO₂Si
• 分子量: 319.519
• InChiKey: SYJNPDISXJEWRJ-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6S)-6-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]piperidin-2-one 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 benzyl (2S)-2-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]piperidine-1-carboxylate
  参考文献：
  名称：

  A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

  摘要：

  A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.090
• 作为产物：
  描述：

  (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 在 palladium on carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (6S)-6-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]piperidin-2-one
  参考文献：
  名称：

  A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

  摘要：

  A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.090

文献信息

• A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine
  作者：Yang Yang、Dean P. Phillips、Shifeng Pan

  DOI：10.1016/j.tetlet.2011.01.090

  日期：2011.4

  A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine. (C) 2011 Elsevier Ltd. All rights reserved.