tert-butyl (2S)-2-[(tert-butyldimethylsilyloxy)methyl]piperidine-1-carboxylate | 1239315-62-8

• 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: tert-butyl (2S)-2-[(tert-butyldimethylsilyloxy)methyl]piperidine-1-carboxylate
• 英文别名: (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-piperidine-1-carboxylate；tert-butyl (2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidine-1-carboxylate
• CAS: 1239315-62-8
• 化学式: C₁₇H₃₅NO₃Si
• 分子量: 329.555
• InChiKey: ISIILXDSUMPLOW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(tert-butyldimethylsilyloxy)methyl]piperidine-1-carboxylate 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(2S)-2-[[(tert-butyldimethylsilyl)oxy]methyl]piperidine
  参考文献：
  名称：

  Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

  摘要：

  A new inhibitor, containing a linked proline-piperidine structure, for the enzyme prolyl oligopeptidase (POP) has been synthesised and demonstrated to bind covalently with the enzyme at the active site. This provides evidence that covalent inhibitors of POP do not have to be limited to structures containing five-membered N-containing heterocyclic rings.

  DOI：

  10.1016/j.bmc.2010.05.012
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (S)-N-Boc-2-哌啶甲醇 在 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以97%的产率得到tert-butyl (2S)-2-[(tert-butyldimethylsilyloxy)methyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

  摘要：

  A new inhibitor, containing a linked proline-piperidine structure, for the enzyme prolyl oligopeptidase (POP) has been synthesised and demonstrated to bind covalently with the enzyme at the active site. This provides evidence that covalent inhibitors of POP do not have to be limited to structures containing five-membered N-containing heterocyclic rings.

  DOI：

  10.1016/j.bmc.2010.05.012

文献信息

• Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation
  作者：Tanveer Mahamadali Shaikh、Arumugam Sudalai

  DOI：10.1002/ejoc.201000169

  日期：——

  An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)-α-conhydrine (98 % ee) and (-)-sedamine (95 % ee), by L -proline-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.

  一种有效的有机催化方法，通过 L-脯氨酸催化的醛的 α-氨基氧基化，对映选择性合成两种重要的哌啶生物碱，即 (+)-α-conhydrine (98% ee) 和 (-)-sedamine (95% ee)已经被开发出来。该策略涉及分子内环化以构建哌啶核心。