4-Hydroxy-2,3-dimethoxy-4-(2-propenyl)-2-cyclobuten-1-one | 124022-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-2,3-dimethoxy-4-(2-propenyl)-2-cyclobuten-1-one
• 英文别名: 4-Hydroxy-2,3-dimethoxy-4-prop-2-enylcyclobut-2-en-1-one
• CAS: 124022-04-4
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: LHESNFPBLHKDTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-2,3-dimethoxy-4-(2-propenyl)-2-cyclobuten-1-one 以 甲苯 为溶剂， 反应 10.0h， 以65%的产率得到1,2-Dimethoxybicyclo<3.2.0>heptane-3,7-dione
  参考文献：
  名称：

  Synthesis of the bicyclo[3.2.0] ring systems from 4-allylcyclobutenones. Intramolecular ketene/alkene cycloadditions

  摘要：

  A general synthesis of bicyclo[3.2.0]heptenones from 4-allylcyclobutenones is described. The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2 + 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety. This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the substitution pattern is conveniently controlled. The scope of the rearrangement and the mechanism are discussed.

  DOI：

  10.1021/jo00021a025
• 作为产物：
  描述：

  3,4-二甲氧基-3-环丁烯-1,2-二酮 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 0.25h， 以71%的产率得到4-Hydroxy-2,3-dimethoxy-4-(2-propenyl)-2-cyclobuten-1-one
  参考文献：
  名称：

  Synthesis of the bicyclo[3.2.0] ring systems from 4-allylcyclobutenones. Intramolecular ketene/alkene cycloadditions

  摘要：

  A general synthesis of bicyclo[3.2.0]heptenones from 4-allylcyclobutenones is described. The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2 + 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety. This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the substitution pattern is conveniently controlled. The scope of the rearrangement and the mechanism are discussed.

  DOI：

  10.1021/jo00021a025

文献信息

• Rearrangements of cyclobutenones. Conversion of selected 4-allylcyclobutenones to bicyclo[3.2.0]heptenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00287a010

  日期：1989.12
• XU, SIMON L.;MOORE, HAROLD W., J. ORG. CHEM., 54,(1989) N6, C. 6018-6021
  作者：XU, SIMON L.、MOORE, HAROLD W.

  DOI：——

  日期：——
• Synthesis of the bicyclo[3.2.0] ring systems from 4-allylcyclobutenones. Intramolecular ketene/alkene cycloadditions
  作者：Simon L. Xu、Haiji Xia、Harold W. Moore

  DOI：10.1021/jo00021a025

  日期：1991.10

  A general synthesis of bicyclo[3.2.0]heptenones from 4-allylcyclobutenones is described. The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2 + 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety. This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the substitution pattern is conveniently controlled. The scope of the rearrangement and the mechanism are discussed.