6-(2-chlorophenyl)-3-(1,3-dithiolan-2-ylidene)-6-methyl-4-phenyl-1,6-dihydropyridin-2(3H)-one | 1434146-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2-chlorophenyl)-3-(1,3-dithiolan-2-ylidene)-6-methyl-4-phenyl-1,6-dihydropyridin-2(3H)-one
• 英文别名: 6-(2-chlorophenyl)-3-(1,3-dithiolan-2-ylidene)-6-methyl-4-phenyl-1H-pyridin-2-one
• CAS: 1434146-81-2
• 化学式: C₂₁H₁₈ClNOS₂
• 分子量: 399.965
• InChiKey: WCNGHCGLLWVRNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1,3-dithiolan-2-ylidene)acetamide 、 2-(2-chlorophenyl)-4-phenylbut-3-yn-2-ol 在 三氟化硼乙醚 、 三氟乙酸 作用下， 反应 0.66h， 以88%的产率得到6-(2-chlorophenyl)-3-(1,3-dithiolan-2-ylidene)-6-methyl-4-phenyl-1,6-dihydropyridin-2(3H)-one
  参考文献：
  名称：

  Regiospecific 6-Endo-Annulation of in Situ Generated 3,4-Dienamides/Acids: Synthesis of δ-Lactams and δ-Lactones

  摘要：

  A novel and efficient method for the construction of alpha-(1,3-dithiolan-2-ylidene) delta-lactam and delta-lactone rings has been developed. It involves the reglospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of alpha-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3 center dot Et2O. A range of alpha-(1,3-dithiolan-2-ylidene) delta-lactams and delta-lactones are obtained in good to high yields. In addition, indenes are prepared by using alpha-acetyl ketene dithioacetal as the precursor.

  DOI：

  10.1021/ol4007772

文献信息

• Regiospecific 6-<i>Endo</i>-Annulation of <i>in Situ </i>Generated 3,4-Dienamides/Acids: Synthesis of δ-Lactams and δ-Lactones
  作者：Ying Liu、Badru-Deen Barry、Haifeng Yu、Jianquan Liu、Peiqiu Liao、Xihe Bi

  DOI：10.1021/ol4007772

  日期：2013.6.7

  A novel and efficient method for the construction of alpha-(1,3-dithiolan-2-ylidene) delta-lactam and delta-lactone rings has been developed. It involves the reglospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of alpha-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3 center dot Et2O. A range of alpha-(1,3-dithiolan-2-ylidene) delta-lactams and delta-lactones are obtained in good to high yields. In addition, indenes are prepared by using alpha-acetyl ketene dithioacetal as the precursor.