3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol | 173913-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol
• 英文别名: 2,6-dimethoxy-3-(2-phenylethynyl)-5-[(E)-1-trimethylsilylbut-1-enyl]benzene-1,4-diol
• CAS: 173913-05-8
• 化学式: C₂₃H₂₈O₄Si
• 分子量: 396.558
• InChiKey: DNNJSQRDZKSLTC-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol 在 potassium carbonate 、 silver(l) oxide 作用下， 以 苯 为溶剂， 生成 2,6-Dimethoxy-3-phenylethynyl-5-((E)-1-trimethylsilanyl-but-1-enyl)-[1,4]benzoquinone
  参考文献：
  名称：

  o-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry

  摘要：

  Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30 degrees C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.

  DOI：

  10.1021/jo951445m
• 作为产物：
  描述：

  4-hydroxy-3-methoxy-2-(phenylethynyl)-4-(1-methoxy-3-(trimethylsilyl)-1,2-hexadienyl)-2-cyclobuten-1-one 以 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol
  参考文献：
  名称：

  o-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry

  摘要：

  Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30 degrees C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.

  DOI：

  10.1021/jo951445m