(1S,3S,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-methyl-3-carboxylic acid methyl ester | 251302-03-1

• 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: (1S,3S,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-methyl-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,3S,4R)-2-benzyl-3-methyl-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 251302-03-1
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: AMWGVQGNVTZRFI-YCPHGPKFSA-N

物化性质

• 沸点：
  331.6±25.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-methyl-3-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到[(1S,3S,4R)-2-benzyl-3-methyl-2-azabicyclo[2.2.1]heptan-3-yl]methanol
  参考文献：
  名称：

  2-氮杂降冰片醇：非常有效的配体，用于钌催化芳族酮的不对称转移加氢

  摘要：

  制备了2-氮杂降冰片基衍生的氨基醇，并将其评估为Ru（II）催化的芳族酮的不对称转移氢化中的配体。为了提高选择性和速率，对配体的结构进行了优化。在40分钟内于94％ee中，使用0.5 mol％的催化剂还原苯乙酮。该体系还能够将多种芳族酮还原为相应的醇，同时保持高对映选择性和产率。检查了催化剂负载和反应容器中助溶剂存在的影响，并进行了线性研究。

  DOI：

  10.1021/jo991914a
• 作为产物：
  描述：

  甲基(1S,3R,4R)-2-氮杂双环[2.2.1]庚烷-3-羧酸酯 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.67h， 生成 (1S,3S,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-methyl-3-carboxylic acid methyl ester
  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

• 2-Azanorbornyl Alcohols:  Very Efficient Ligands for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones
  作者：Diego A. Alonso、Sofia J. M. Nordin、Peter Roth、Tibor Tarnai、Pher G. Andersson、Marc Thommen、Ulrich Pittelkow

  DOI：10.1021/jo991914a

  日期：2000.5.1

  2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized. Acetophenone was reduced using 0.5 mol % catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alcohols, while maintaining

  制备了2-氮杂降冰片基衍生的氨基醇，并将其评估为Ru（II）催化的芳族酮的不对称转移氢化中的配体。为了提高选择性和速率，对配体的结构进行了优化。在40分钟内于94％ee中，使用0.5 mol％的催化剂还原苯乙酮。该体系还能够将多种芳族酮还原为相应的醇，同时保持高对映选择性和产率。检查了催化剂负载和反应容器中助溶剂存在的影响，并进行了线性研究。
• 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%.