2-<4-(N,N-dimethylamino)phenyl>-6-(2-pyridyl)-4H-thiopyran-4-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-<4-(N,N-dimethylamino)phenyl>-6-(2-pyridyl)-4H-thiopyran-4-one
• 英文别名: 2-[4-(Dimethylamino)phenyl]-6-pyridin-2-ylthiopyran-4-one
• 化学式: C₁₈H₁₆N₂OS
• 分子量: 308.404
• InChiKey: QDHKCFWWOBHINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-(dimethylamino)benzodithioate 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 2-<4-(N,N-dimethylamino)phenyl>-6-(2-pyridyl)-4H-thiopyran-4-one
  参考文献：
  名称：

  Synthesis of 2,6-diaryl-4H-thiopyran-4-ones

  摘要：

  A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed. The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters. The intermediate beta-thioxo ketone from the first condensation was converted to the corresponding beta-(methylthio) enone for both protection and reactivity purposes. Facile addition-elimination of the methylthio moiety by a beta-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle. This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.

  DOI：

  10.1021/jo00063a023

文献信息

• Boaz Neil W., Fox Kristine M., J. Org. Chem., 58 (1993) N 11, S 3042-3045
  作者：Boaz Neil W., Fox Kristine M.

  DOI：——

  日期：——
• Synthesis of 2,6-diaryl-4H-thiopyran-4-ones
  作者：Neil W. Boaz、Kristine M. Fox

  DOI：10.1021/jo00063a023

  日期：1993.5

  A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed. The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters. The intermediate beta-thioxo ketone from the first condensation was converted to the corresponding beta-(methylthio) enone for both protection and reactivity purposes. Facile addition-elimination of the methylthio moiety by a beta-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle. This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.