(2S,2'S)-N,N'-[(2S,3S)-1,4-bis(benzyloxy)butane-2,3-diyl]bis[2-(4-isobutylphenyl)propanamide] | 1404096-10-1

• 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: (2S,2'S)-N,N'-[(2S,3S)-1,4-bis(benzyloxy)butane-2,3-diyl]bis[2-(4-isobutylphenyl)propanamide]
• CAS: 1404096-10-1
• 化学式: C₄₄H₅₆N₂O₄
• 分子量: 676.94
• InChiKey: OKPXRYIXCVSTMI-LFHSECSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.39
• 重原子数：
  50.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-N,N'-[(2S,3S)-1,4-bis(benzyloxy)butane-2,3-diyl]bis[2-(4-isobutylphenyl)propanamide] 在 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (4S,4'S)-2,2'-bis[(1S)-1-(4-isobutylphenyl)ethyl]-4,4',5,5'-tetrahydro-4,4'-bi-1,3-oxazole
  参考文献：
  名称：

  Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid

  摘要：

  Novel C-2-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination.

  DOI：

  10.1055/s-0031-1289811
• 作为产物：
  描述：

  (R)-(-)-布洛芬 、 (2S,3S)-1,4-bis(benzyloxy)butane-2,3-diamine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.25h， 以90%的产率得到(2S,2'S)-N,N'-[(2S,3S)-1,4-bis(benzyloxy)butane-2,3-diyl]bis[2-(4-isobutylphenyl)propanamide]
  参考文献：
  名称：

  Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid

  摘要：

  Novel C-2-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination.

  DOI：

  10.1055/s-0031-1289811