2-phenyl-3,4,4-trimethoxy-2-cyclobuten-1-one | 144790-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenyl-3,4,4-trimethoxy-2-cyclobuten-1-one
• 英文别名: 3,4,4-Trimethoxy-2-phenylcyclobut-2-en-1-one
• CAS: 144790-80-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: RVGDTFWCIQYBHK-UHFFFAOYSA-N

物化性质

• 沸点：
  366.6±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-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 0.75h， 生成 1-hydroxy-1,2-diphenyl-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
• 作为产物：
  描述：

  3,4-二甲氧基-3-环丁烯-1,2-二酮 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-phenyl-3,4,4-trimethoxy-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

• Cyclobutenone Ethylenedithioacetals and Their Ready Electrocyclic Ring Opening
  作者：Ernst Schaumann、Harold Moore、Wilko Regenhardt

  DOI：10.1055/s-2001-14559

  日期：——

  substi- tuted p-quinones. 4,5 Our interest in organosulfur derivatives of cyclobutenones 6 led us to investigate the chemistry of cy- clobutenone dithioacetals. In particular, we were interest- ed in 1,3-dithiolane derivatives because of their potential utility for the generation of cyclobutenediones via a base induced [3 + 2] cycloreversion reaction. 7 Reported herein is an efficient preparation of cy- clobutenedione

  论文 Cyclobutenone Ethylenedithioacetals and their Ready Electrocyclic Ring opening a Synthesi and 随后开环 Cyclobutenone Ethylen d Regenhardt, Wilko ithioacetals Ernst Schaumann,* a Harold W. Moore* ba Institut fur Organische Chemie, Technische Universitat Clausthal, Leibnizstrase 6, 38678 Clausthal- Zellerfeld，德国传真 [phone]；电子邮件：[e-mail] b 加州大学欧文分校化学系，欧文，CA 92697–2025，美国 传真
• 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.