5-(1-(naphthalen-1-yl)-2-nitroethyl)furan-2(5H)-one | 1140282-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(1-(naphthalen-1-yl)-2-nitroethyl)furan-2(5H)-one
• 英文别名: (2R)-2-[(1R)-1-naphthalen-1-yl-2-nitroethyl]-2H-furan-5-one
• CAS: 1140282-13-8
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: OLKZZSIKRVWEGP-LSDHHAIUSA-N

物化性质

• 沸点：
  539.7±33.0 °C(predicted)
• 密度：
  1.336±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  β-(1-naphthyl)nitroethylene 、 2(5H)-呋喃酮 在 C₄₅H₅₂N₂O₃Zn₂ 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到5-(1-(naphthalen-1-yl)-2-nitroethyl)furan-2(5H)-one
  参考文献：
  名称：

  Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous Nucleophilicity under Dinuclear Zinc Catalysis

  摘要：

  Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.

  DOI：

  10.1021/ja809723u

文献信息

• Inverting the Diastereoselectivity of the Mukaiyama–Michael Addition with Graphite-Based Catalysts
  作者：Maria Rosaria Acocella、Marco Mauro、Laura Falivene、Luigi Cavallo、Gaetano Guerra

  DOI：10.1021/cs401053t

  日期：2014.2.7

  Here, we show that graphite-based catalysts, mainly graphite oxide (GO) and exfoliated GO, are effective recyclable catalysts for a relevant stereoselective Mukaiyama-Michael addition, outperforming currently available catalysts. Moreover, the graphite-based catalysts described here invert the diastereoselectivity relative to that observed with known catalysts, with the unprecedented large prevalence of the anti diastereoisomer. This inverted diastereoselectivity is increased when the catalyst concentration is reduced and after catalyst recycling. Density functional theory calculations suggest that the selectivity is determined by two types of supramolecular interactions operating between the catalyst and the substrates at the diastereoselectivity-determining transition state, specifically, the pi-stacking of beta-nitrostyrene with graphite and the van der Waals interaction between the SiMe3 group of the silyl ether and the graphite.