1-hydroxy-1-(1-hexynyl)-2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobutene | 144790-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxy-1-(1-hexynyl)-2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobutene
• 英文别名: 1-Hex-1-ynyl-4,4-dimethoxy-3-methyl-2-phenylcyclobut-2-en-1-ol
• CAS: 144790-88-5
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: UCAFQUSPGJWPQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1-(1-hexynyl)-2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobutene 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 0.25h， 生成 4-Hex-1-ynyl-4-hydroxy-2-methyl-3-phenyl-cyclobut-2-enone
  参考文献：
  名称：

  A potentially general regiospecific synthesis of substituted quinones from dimethyl squarate

  摘要：

  A potentially general regiospecific synthesis of benzo- and naphthoquinones is described. This method starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5. Addition of an alkynyl-, alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl- 4-alkenyl- or 4-aryl-4-hydroxycyclobutenones 7-9, and these readily rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene. In a similar fashion, 15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones.

  DOI：

  10.1021/jo00051a040
• 作为产物：
  描述：

  2-phenyl-3,4,4-trimethoxy-2-cyclobuten-1-one 在 正丁基锂 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 1-hydroxy-1-(1-hexynyl)-2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobutene
  参考文献：
  名称：

  A potentially general regiospecific synthesis of substituted quinones from dimethyl squarate

  摘要：

  A potentially general regiospecific synthesis of benzo- and naphthoquinones is described. This method starts with dimethyl squarate (1), which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5. Addition of an alkynyl-, alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl- 4-alkenyl- or 4-aryl-4-hydroxycyclobutenones 7-9, and these readily rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene. In a similar fashion, 15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones.

  DOI：

  10.1021/jo00051a040