(E)-1-((4-methoxybenzyl)oxy)-2-(2-nitrovinyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-((4-methoxybenzyl)oxy)-2-(2-nitrovinyl)benzene
• 英文别名: 1-[(4-methoxyphenyl)methoxy]-2-[(E)-2-nitroethenyl]benzene
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: DONYYEMHSGBOOE-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 3-((4-methoxyphenyl)thio)-2-methyl-3-oxopropanoate 、 (E)-1-((4-methoxybenzyl)oxy)-2-(2-nitrovinyl)benzene 在 C₂₈H₂₆F₆N₄O 作用下， 以 均三甲苯 为溶剂， 反应 48.0h， 以99%的产率得到
  参考文献：
  名称：

  Organocatalytic Route to Dihydrocoumarins and Dihydroquinolinones in All Stereochemical Configurations

  摘要：

  A straightforward stereodivergent route to dihydrocoumarins and dihydroquinolinones based on cinchona alkaloid catalyzed addition reactions of monothiomalonates (MTMs) to functionalized nitroolefins followed by deprotection and chemoselective cyclization has been developed. The synthesis proceeds under mild conditions and yields heterocycles with adjacent quaternary and tertiary stereogenic centers in very high yields and stereoselectivities. Moreover, full control over the relative and absolute configuration is achieved by the use of (pseudo)enantiomeric catalysts and the difference in reactivity of thioester versus oxoester moieties.

  DOI：

  10.1021/ol502697s
• 作为产物：
  描述：

  4-甲氧基氯苄 在 ammonium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E)-1-((4-methoxybenzyl)oxy)-2-(2-nitrovinyl)benzene
  参考文献：
  名称：

  Organocatalytic Route to Dihydrocoumarins and Dihydroquinolinones in All Stereochemical Configurations

  摘要：

  A straightforward stereodivergent route to dihydrocoumarins and dihydroquinolinones based on cinchona alkaloid catalyzed addition reactions of monothiomalonates (MTMs) to functionalized nitroolefins followed by deprotection and chemoselective cyclization has been developed. The synthesis proceeds under mild conditions and yields heterocycles with adjacent quaternary and tertiary stereogenic centers in very high yields and stereoselectivities. Moreover, full control over the relative and absolute configuration is achieved by the use of (pseudo)enantiomeric catalysts and the difference in reactivity of thioester versus oxoester moieties.

  DOI：

  10.1021/ol502697s

文献信息

• Organocatalytic Route to Dihydrocoumarins and Dihydroquinolinones in All Stereochemical Configurations
  作者：Oliver D. Engl、Sven P. Fritz、Alexander Käslin、Helma Wennemers

  DOI：10.1021/ol502697s

  日期：2014.10.17

  A straightforward stereodivergent route to dihydrocoumarins and dihydroquinolinones based on cinchona alkaloid catalyzed addition reactions of monothiomalonates (MTMs) to functionalized nitroolefins followed by deprotection and chemoselective cyclization has been developed. The synthesis proceeds under mild conditions and yields heterocycles with adjacent quaternary and tertiary stereogenic centers in very high yields and stereoselectivities. Moreover, full control over the relative and absolute configuration is achieved by the use of (pseudo)enantiomeric catalysts and the difference in reactivity of thioester versus oxoester moieties.