3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenyl-3,6-dihydro-2H-pyran-2-one | 1434146-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenyl-3,6-dihydro-2H-pyran-2-one
• 英文别名: 3-(1,3-Dithiolan-2-ylidene)-6-methyl-4,6-diphenylpyran-2-one；3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenylpyran-2-one
• CAS: 1434146-78-7
• 化学式: C₂₁H₁₈O₂S₂
• 分子量: 366.505
• InChiKey: XZKNNEYWFHHHIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 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：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-dithiolan-2-ylideneacetic acid 、 2,4-二苯基-3-丁炔-2-醇 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以91%的产率得到3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenyl-3,6-dihydro-2H-pyran-2-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.