(1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(aminomethyl)-2-azabicyclo[2,2,1]heptane | 1290085-13-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(aminomethyl)-2-azabicyclo[2,2,1]heptane
• 英文别名: [(1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-3-yl]methanamine
• CAS: 1290085-13-0
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: VZUATBHEHMNOTC-PMOUVXMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(aminomethyl)-2-azabicyclo[2,2,1]heptane 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(benzylaminomethyl)-2-azabicyclo[2,2,1]heptane
  参考文献：
  名称：

  New 2-azanorbornyl derivatives: chiral (N,N)-donating ligands for asymmetric catalysis

  摘要：

  New chiral 2-azanorbornane derivatives were prepared and used as (N,N)-donating ligands in a copper-catalyzed Henry reaction yielding up to 62% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.011
• 作为产物：
  描述：

  (1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(azidomethyl)-2-azabicyclo[2,2,1]heptane 在 三苯基膦 作用下， 以 甲醇 为溶剂， 以56%的产率得到(1S,3S,4R)-2-[(S)-1-phenylethyl]-3-(aminomethyl)-2-azabicyclo[2,2,1]heptane
  参考文献：
  名称：

  New 2-azanorbornyl derivatives: chiral (N,N)-donating ligands for asymmetric catalysis

  摘要：

  New chiral 2-azanorbornane derivatives were prepared and used as (N,N)-donating ligands in a copper-catalyzed Henry reaction yielding up to 62% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.011

文献信息

• Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions
  作者：Elżbieta Wojaczyńska、Jacek Skarżewski、Łukasz Sidorowicz、Robert Wieczorek、Jacek Wojaczyński

  DOI：10.1039/c6nj02251k

  日期：——

  Chiral scaffolds of 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane were used for the construction of new modular catalysts containing complexing moieties pyridine, 2,2′-bipyridine and 1,10-phenanthroline appended by an imine linkage. The coordination abilities of the new ligands towards Zn(II) were investigated using NMR and UV spectroscopy. The plausible structures of the [ZnL2]2+ and [ZnLXn](2−n)+

  2-氮杂双环[2.2.1]庚烷和2-氮杂双环[3.2.1]辛烷的手性支架用于构建新的模块催化剂，该催化剂包含配位吡啶，2,2'-联吡啶和1,10-菲咯啉亚胺键。利用NMR和UV光谱研究了新配体对Zn（II）的配位能力。通过比较实验和DFT计算的NMR光谱，可以确定形成的[ZnL 2 ] 2+和[ZnLX n ] （2- n）+配合物的合理结构。[ZnLX n ] （2- n）+的催化应用在与芳族醛酮的不对称醛醇缩合反应型复合物所产生的过量的相应的顺式中高达> 98％ee的-aldols。
• New 2-azanorbornyl derivatives: chiral (N,N)-donating ligands for asymmetric catalysis
  作者：Elżbieta Wojaczyńska

  DOI：10.1016/j.tetasy.2010.12.011

  日期：2011.1

  New chiral 2-azanorbornane derivatives were prepared and used as (N,N)-donating ligands in a copper-catalyzed Henry reaction yielding up to 62% ee. (C) 2010 Elsevier Ltd. All rights reserved.