2,2,3-三甲氧基-3-环丁烯-1-酮 | 68057-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2,3-三甲氧基-3-环丁烯-1-酮
• 英文名称: 2,2,3-trimethoxy-3-cyclobuten-1-one
• 英文别名: 3,4,4-trimethoxy-2-cyclobutenone；3,4,4-Trimethoxy-cyclobut-2-enon；3,4,4-Trimethoxycyclobut-2-en-1-one
• CAS: 68057-55-6
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: OAAULVKMECGMOV-UHFFFAOYSA-N

物化性质

• 沸点：
  58-62 °C(Press: 0.25 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,3,4,4-tetramethoxy-2-(trimethylsilyl)cyclobutanone 反应 24.0h， 以80%的产率得到2,2,3-三甲氧基-3-环丁烯-1-酮
  参考文献：
  名称：

  Cycloaddition of (trimethylsilyl)ketene with tetraalkoxyethylenes

  摘要：

  DOI：

  10.1021/jo01292a038

文献信息

• Synthesen von Moniliformin, einem Mycotoxin mit Cyclobutendion-Struktur
  作者：Daniel Bellu?、Hanspeter Fischer、Hans Greuter、Pierre Martin

  DOI：10.1002/hlca.19780610526

  日期：1978.7.12

  Syntheses of Moniliformin, a Mycotoxine with a Cyclobutenedione Structure

  具有环丁二酮结构的霉菌毒素莫尼西丁的合成
• BRADY W. T.; SAIDI K., J. ORG. CHEM., 1980, 45, NO 4, 727-729
  作者：BRADY W. T.、 SAIDI K.

  DOI：——

  日期：——
• ABEN R. W.; SCHEEREN H. W., J. CHEM. SOC. PERKIN TRANS., 1979, PART 1, NO 12, 3132-3138
  作者：ABEN R. W.、 SCHEEREN H. W.

  DOI：——

  日期：——
• Cycloaddition of (trimethylsilyl)ketene with tetraalkoxyethylenes
  作者：William T. Brady、Kazem Saidi

  DOI：10.1021/jo01292a038

  日期：1980.2
• 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.