2,3-dimethoxy-4-hydroxy-4-(1-methoxy-3-(trimethylsilyl)-1,2-hexadienyl)-2-cyclobuten-1-one | 572916-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dimethoxy-4-hydroxy-4-(1-methoxy-3-(trimethylsilyl)-1,2-hexadienyl)-2-cyclobuten-1-one
• CAS: 572916-14-4
• 化学式: C₁₆H₂₆O₅Si
• 分子量: 326.465
• InChiKey: VOJDTLGZXTWMKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-4-hydroxy-4-(1-methoxy-3-(trimethylsilyl)-1,2-hexadienyl)-2-cyclobuten-1-one 在 potassium carbonate 、 silver(l) oxide 作用下， 以 甲苯 、 苯 为溶剂， 反应 7.0h， 生成 3,5,6-trimethoxy-2-(1-(trimethylsilyl)-1(E)-butenyl)-2,5-cyclohexadiene-1,4-dione
  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：

  3,4-二甲氧基-3-环丁烯-1,2-二酮 、 1-methoxy-3-(trimethylsilyl)-1,2-hexadiene 在 正丁基锂 作用下， 生成 2,3-dimethoxy-4-hydroxy-4-(1-methoxy-3-(trimethylsilyl)-1,2-hexadienyl)-2-cyclobuten-1-one
  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

文献信息

• <i>o</i>-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry
  作者：Meng Taing、Harold W. Moore

  DOI：10.1021/jo951445m

  日期：1996.1.1

  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.