((2R,3S)-3-((2-aminophenylamino)methyl)bicyclo[2.2.1]heptan-2-yl)methanol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ((2R,3S)-3-((2-aminophenylamino)methyl)bicyclo[2.2.1]heptan-2-yl)methanol
• 英文别名: [(1R,2R,3S,4S)-3-[(2-aminoanilino)methyl]-2-bicyclo[2.2.1]heptanyl]methanol
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: BQPCKPHELGEBTP-QNWHQSFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ((2R,3S)-3-((2-aminophenylamino)methyl)bicyclo[2.2.1]heptan-2-yl)methanol
  参考文献：
  名称：

  Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde

  摘要：

  The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. The chiral ligands were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, arylamine and tosyl substituted chiral ligands 9a-d exhibited the highest selectivities (up to 97% ee). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.019

文献信息

• Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
  作者：Cihangir Tanyeli、Serhat Odabaş、Mine Erdem、Esen Çakır、Eda Keskin

  DOI：10.1016/j.tetasy.2007.09.019

  日期：2007.9

  The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. The chiral ligands were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, arylamine and tosyl substituted chiral ligands 9a-d exhibited the highest selectivities (up to 97% ee). (c) 2007 Elsevier Ltd. All rights reserved.