methyl (1S,3R,4R)-2-benzyl-3-[hydroxy(phenyl)methyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate | 251302-09-7

• 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: methyl (1S,3R,4R)-2-benzyl-3-[hydroxy(phenyl)methyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 251302-09-7
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: FJDCBGHJLVUXMB-XQXKNUKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1S,3R,4R)-2-benzyl-3-[hydroxy(phenyl)methyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成
  参考文献：
  名称：

  Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles

  摘要：

  A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.

  DOI：

  10.1021/ol990942c
• 作为产物：
  描述：

  methyl (1R,3R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， -20.0~20.0 ℃ 、709.32 kPa 条件下， 反应 0.67h， 生成 methyl (1S,3R,4R)-2-benzyl-3-[hydroxy(phenyl)methyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles

  摘要：

  A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.

  DOI：

  10.1021/ol990942c

文献信息

• Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles
  作者：Diego A. Alonso、Sofia J. M. Nordin、Pher G. Andersson

  DOI：10.1021/ol990942c

  日期：1999.11.1

  A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.