3-n-butyl-4,4-dimethoxy-2-cyclobuten-1-one | 144791-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-n-butyl-4,4-dimethoxy-2-cyclobuten-1-one
• 英文别名: 3-Butyl-4,4-dimethoxycyclobut-2-en-1-one
• CAS: 144791-05-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: PUYVRHLYFUIEGO-UHFFFAOYSA-N

物化性质

• 沸点：
  264.4±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-n-butyl-4,4-dimethoxy-2-cyclobuten-1-one 在 盐酸 、 叔丁基锂 作用下， 以 氯仿 为溶剂， 反应 1.83h， 生成 2-Butyl-4-hydroxy-4-isopropenyl-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：

  2,2,3-三甲氧基-3-环丁烯-1-酮 在 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 3-n-butyl-4,4-dimethoxy-2-cyclobuten-1-one
  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

文献信息

• A potentially general regiospecific synthesis of substituted quinones from dimethyl squarate
  作者：Leah M. Gayo、Michael P. Winters、Harold W. Moore

  DOI：10.1021/jo00051a040

  日期：1992.12

  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.