(-)-(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-(benzylaminomethyl)-2-azabicyclo[2.2.1]heptane | 1290085-14-1

• 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: (-)-(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-(benzylaminomethyl)-2-azabicyclo[2.2.1]heptane
• 英文别名: N-benzyl-1-[(1S,3R,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-3-yl]methanamine
• CAS: 1290085-14-1
• 化学式: C₂₂H₂₈N₂
• 分子量: 320.478
• InChiKey: OQMWKLHZAHGZQZ-XGARDCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminemethyl-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,3R,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
• 作为试剂：
  描述：

  苯甲醛 、 硝基乙烷 在 (-)-(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-(benzylaminomethyl)-2-azabicyclo[2.2.1]heptane 、 copper(II) acetate monohydrate 作用下， 以 异丙醇 为溶剂， 生成 rac-(1R,2S)-2-nitro-1-phenylpropan-1-ol 、 (1R,2S)-2-nitro-1-phenylpropan-1-ol 、 2-nitro-1-phenylpropan-1-ol 、 (1R,2R)-2-nitro-1-phenylpropan-1-ol
  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

• Chiral pyrrolidine thioethers and 2-azanorbornane derivatives bearing additional nitrogen functions. Enantiopure ligands for palladium-catalyzed Tsuji-Trost reaction
  作者：Elżbieta Wojaczyńska、Karolina Kamińska、Jacek Wojaczyński、Jacek Skarżewski

  DOI：10.3998/ark.5550190.p009.792

  日期：——

  An efficient procedure for the synthesis of new enantiopure pyrrolidine-based sulfides bearing additional nitrogen donors and secondary amines based on a bicyclic 2-azanorbornane skeleton was developed. Their application as ligands in palladium-catalyzed Tsuji-Trost reactions led to high yields and up to 82% ee.

  开发了一种基于双环 2-氮杂降冰片烷骨架合成带有额外氮供体和仲胺的新型对映纯吡咯烷基硫化物的有效方法。它们在钯催化的 Tsuji-Trost 反应中作为配体的应用导致高产率和高达 82% 的 ee。
• 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.