(2R,5S)-1-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxy)-2-(propa-1,2-dienyl)piperidine | 1242338-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5S)-1-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxy)-2-(propa-1,2-dienyl)piperidine
• CAS: 1242338-31-3
• 化学式: C₂₂H₃₃NO₃Si
• 分子量: 387.594
• InChiKey: JYFBKQJZMMALSE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (2R,5S)-1-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxy)-2-(propa-1,2-dienyl)piperidine 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以52%的产率得到(3S,6S)-6-丙基哌啶-3-醇
  参考文献：
  名称：

  Synthesis of functionalized 3-hydroxypiperidines

  摘要：

  The synthetic versatility of three chemoenzymatically prepared hydroxypiperidine building blocks has been explored, resulting in a library of enantiopure functionalized piperidines. Key steps involved N-acyliminium ion-mediated CC-bond formation and cross-metathesis reactions, after which full deprotection led to the set of free 3-hydroxypiperidines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.089
• 作为产物：
  描述：

  炔丙基三甲基硅烷 、 benzyl (5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxypiperidine-1-carboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以44 mg的产率得到(2R,5S)-1-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxy)-2-(propa-1,2-dienyl)piperidine
  参考文献：
  名称：

  Synthesis of functionalized 3-hydroxypiperidines

  摘要：

  The synthetic versatility of three chemoenzymatically prepared hydroxypiperidine building blocks has been explored, resulting in a library of enantiopure functionalized piperidines. Key steps involved N-acyliminium ion-mediated CC-bond formation and cross-metathesis reactions, after which full deprotection led to the set of free 3-hydroxypiperidines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.089

文献信息

• Synthesis of functionalized 3-hydroxypiperidines
  作者：Marloes A. Wijdeven、Floris L. van Delft、Floris P.J.T. Rutjes

  DOI：10.1016/j.tet.2010.05.089

  日期：2010.7

  The synthetic versatility of three chemoenzymatically prepared hydroxypiperidine building blocks has been explored, resulting in a library of enantiopure functionalized piperidines. Key steps involved N-acyliminium ion-mediated CC-bond formation and cross-metathesis reactions, after which full deprotection led to the set of free 3-hydroxypiperidines. (C) 2010 Elsevier Ltd. All rights reserved.