(4S,4'S)-2,2'-bis[(1R)-1-(6-methoxy-2-naphthyl)ethyl]-4,4',5,5'-tetrahydro-4,4'-bi-1,3-oxazole | 1404096-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,4'S)-2,2'-bis[(1R)-1-(6-methoxy-2-naphthyl)ethyl]-4,4',5,5'-tetrahydro-4,4'-bi-1,3-oxazole
• 英文别名: (4S)-2-[(1R)-1-(6-methoxynaphthalen-2-yl)ethyl]-4-[(4S)-2-[(1R)-1-(6-methoxynaphthalen-2-yl)ethyl]-4,5-dihydro-1,3-oxazol-4-yl]-4,5-dihydro-1,3-oxazole
• CAS: 1404096-23-6
• 化学式: C₃₂H₃₂N₂O₄
• 分子量: 508.617
• InChiKey: UBZVYJIKRUPAPU-XYTTVBAYSA-N

物化性质

• 沸点：
  675.6±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  萘普生 在 palladium 10% on activated carbon 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、413.7 kPa 条件下， 反应 186.25h， 生成 (4S,4'S)-2,2'-bis[(1R)-1-(6-methoxy-2-naphthyl)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

文献信息

• Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid
  作者：Venkitasamy Kesavan、Kaluvu Balaraman、Ravichandran Vasanthan

  DOI：10.1055/s-0031-1289811

  日期：2012.8

  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.