(Z)-1-naphthalen-1-yl-3-phenylprop-2-en-1-one | 62918-21-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-1-naphthalen-1-yl-3-phenylprop-2-en-1-one
• CAS: 62918-21-2
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: RSYVUCWGXLBPOV-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-萘乙酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (Z)-1-naphthalen-1-yl-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Bonsignore,L. et al., Gazzetta Chimica Italiana, 1976, vol. 106, p. 617 - 624

  摘要：

  DOI：

文献信息

• Enantioselective Diels–Alder Reactions of Cyclohexa-1,3-diene and Chalcones Catalyzed by Intramolecular Silicon–Sulfur Lewis Pairs as Chiral Lewis Acids
  作者：Polina Shaykhutdinova、Martin Oestreich

  DOI：10.1021/acs.organomet.6b00548

  日期：2016.8.22

  The stereoselective preparation of diastereomeric dihydrosilepine-derived silicon cations decorated with another binaphthyl unit at the silicon atom is described. A sulfide donor attached to that additional binaphthyl substituent forms an intramolecular Lewis pair with the electron-deficient silicon atom, as verified by Si-29 NMR spectroscopy. Both chiral sulfur-stabilized silicon cations act as catalysts in the difficult Diels Alder reaction of cydohexa-1,3-diene and chalcone derivatives. Both Lewis acids induce enantioselectivity, but the S,S relative configuration is superior to the S,R configuration. With the former diastereomer, enantiomeric excesses of close to 60% are obtained. These values are the highest achieved to date in this seemingly trivial cycloaddition.