(4R,4'R)-2,2'-bis[(1R)-1-(6-methoxy-2-naphthyl)ethyl]-4,4',5,5'-tetrahydro-4,4'-bi-1,3-oxazole | 1404096-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4R,4'R)-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: (4R)-2-[(1R)-1-(6-methoxynaphthalen-2-yl)ethyl]-4-[(4R)-2-[(1R)-1-(6-methoxynaphthalen-2-yl)ethyl]-4,5-dihydro-1,3-oxazol-4-yl]-4,5-dihydro-1,3-oxazole
• CAS: 1404096-25-8
• 化学式: C₃₂H₃₂N₂O₄
• 分子量: 508.617
• InChiKey: UBZVYJIKRUPAPU-AVRWMQKNSA-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， 反应 90.25h， 生成 (4R,4'R)-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
• 作为试剂：
  描述：

  N-亚苄基-4-甲氧基苯胺 、 苯乙炔 在 copper(II) perchlorate hexahydrate 、 (4R,4'R)-2,2'-bis[(1R)-1-(6-methoxy-2-naphthyl)ethyl]-4,4',5,5'-tetrahydro-4,4'-bi-1,3-oxazole 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以27%的产率得到
  参考文献：
  名称：

  酒石酸衍生的双齿生物杂唑啉在末端炔烃向亚胺对映选择性加成中的应用

  摘要：

  易于从酒石酸合成一系列高效且廉价的生物恶唑啉配体，并进一步探索了将末端炔烃与铜（II）盐组合对映选择性加成至亚胺的方法。这是有史以来第一个报告，显示双齿生物x唑啉配体在具有良好对映选择性的炔丙基胺合成中的应用。

  DOI：

  10.1016/j.tetlet.2013.04.108

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.