4-methoxy-6-(pyridin-3-yl)-5,6-dihydro-2H-pyran-2-one | 1006691-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methoxy-6-(pyridin-3-yl)-5,6-dihydro-2H-pyran-2-one
• CAS: 1006691-27-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: YQHKPRFUKKKMAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 甲醇 、 2,3-丁二烯酸甲酯 在 正丁基锂 、 三甲基膦 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以44%的产率得到4-methoxy-6-(pyridin-3-yl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Alcohol-Assisted Phosphine Catalysis:  One-Step Syntheses of Dihydropyrones from Aldehydes and Allenoates

  摘要：

  This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.

  DOI：

  10.1021/ol702462w

文献信息

• Alcohol-Assisted Phosphine Catalysis:  One-Step Syntheses of Dihydropyrones from Aldehydes and Allenoates
  作者：Gardner S. Creech、Ohyun Kwon

  DOI：10.1021/ol702462w

  日期：2008.2.1

  This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.