(E)-3-hydroxy-2,3-dimethyl-1-nitrohept-1-en-5-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-hydroxy-2,3-dimethyl-1-nitrohept-1-en-5-one
• 英文别名: (E)-5-hydroxy-5,6-dimethyl-7-nitrohept-6-en-3-one
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: RKQPHFHEDZQNAE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-methyl-4-nitrobut-3-ene-2-one 、 丁酮 在 溶剂黄146 、 lithium diisopropyl amide 作用下， 生成 (E)-3-hydroxy-2,3-dimethyl-1-nitrohept-1-en-5-one
  参考文献：
  名称：

  Addition of Ketone and Ester Lithium Enolates to (E)-.beta.-Nitroenones

  摘要：

  Under kinetic control at -78 degrees C, reactions of ketone or ester lithium enolates with (E)-beta-nitroenones 2 occurred at the carbonyl group giving (E)-3-hydroxy-5-nitroalk-4-enones 6 or (E)-3-hydroxy-5-nitroalk-4-enoates 13, respectively, with good regioselectivity. When the temperature of the reaction between 2 and lithium ketone enolates was allowed to warm up to -10 degrees C before hydrolysis, solely the 2-(nitromethyl) 1,4-diketones 8 were obtained. Steric factors which might influence the observed stereoselectivities during the nucleophilic attack on beta-nitroenones are discussed.

  DOI：

  10.1021/jo00125a027

文献信息

• Addition of Ketone and Ester Lithium Enolates to (E)-.beta.-Nitroenones
  作者：Raphaeel Schneider、Philippe Gerardin、Bernard Loubinoux

  DOI：10.1021/jo00125a027

  日期：1995.10

  Under kinetic control at -78 degrees C, reactions of ketone or ester lithium enolates with (E)-beta-nitroenones 2 occurred at the carbonyl group giving (E)-3-hydroxy-5-nitroalk-4-enones 6 or (E)-3-hydroxy-5-nitroalk-4-enoates 13, respectively, with good regioselectivity. When the temperature of the reaction between 2 and lithium ketone enolates was allowed to warm up to -10 degrees C before hydrolysis, solely the 2-(nitromethyl) 1,4-diketones 8 were obtained. Steric factors which might influence the observed stereoselectivities during the nucleophilic attack on beta-nitroenones are discussed.