dispiro[4.1.4.1]dodeca-2,9-diene-6,12-dione | 1049016-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dispiro[4.1.4.1]dodeca-2,9-diene-6,12-dione
• 英文别名: dispiro[4.1.47.15]dodeca-2,9-diene-6,12-dione
• CAS: 1049016-53-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: XLFPQMQEGMCEOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dispiro[4.1.4.1]dodeca-2,9-diene-6,12-dione 在 sodium methylate 、 N,N-二甲基甲酰胺 作用下， 反应 0.08h， 以5.8%的产率得到methyl 1-(cyclopent-3-enecarbonyl)cyclopent-3-enecarboxylate
  参考文献：
  名称：

  Insights into the Formation of Symmetrical Trimers of Dialkylated Ketenes Starting from Acid Chloride Precursors

  摘要：

  Application of known dialkyl ketene di- and trimerization to more complex precursors could readily open the route to highly functionalized symmetrical cyclobuta-1,3-diones and cyclohexa-1,3,5-triones. We report herein the results on three substrates containing either a C=C double bond or a protected glycol moiety as illustrative functionalized groups. The nature of the substituents is found to be crucial: while cyclopentenyl and more constrained dioxolanocyclopentenyl precursors efficiently dimerize, a diallylic derivative fails. At the millimolar scale, methoxide-catalyzed trimerization shows limited reproducibility, even for the reported substrate tetramethylcyclobuta-1,3-dione. However, systematic studies, including the use of microwaves, demonstrate that formation of symmetrical trimers is favored under solvent-free conditions and conventional heating, which allowed us to isolate and characterize trispiro[4.1.4.1.4.1]octadeca-2,9,15-triene-6,12,18-trione.

  DOI：

  10.1007/s00706-007-0689-z
• 作为产物：
  描述：

  cyclopent-3-ene carbonyl chloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到dispiro[4.1.4.1]dodeca-2,9-diene-6,12-dione
  参考文献：
  名称：

  Insights into the Formation of Symmetrical Trimers of Dialkylated Ketenes Starting from Acid Chloride Precursors

  摘要：

  Application of known dialkyl ketene di- and trimerization to more complex precursors could readily open the route to highly functionalized symmetrical cyclobuta-1,3-diones and cyclohexa-1,3,5-triones. We report herein the results on three substrates containing either a C=C double bond or a protected glycol moiety as illustrative functionalized groups. The nature of the substituents is found to be crucial: while cyclopentenyl and more constrained dioxolanocyclopentenyl precursors efficiently dimerize, a diallylic derivative fails. At the millimolar scale, methoxide-catalyzed trimerization shows limited reproducibility, even for the reported substrate tetramethylcyclobuta-1,3-dione. However, systematic studies, including the use of microwaves, demonstrate that formation of symmetrical trimers is favored under solvent-free conditions and conventional heating, which allowed us to isolate and characterize trispiro[4.1.4.1.4.1]octadeca-2,9,15-triene-6,12,18-trione.

  DOI：

  10.1007/s00706-007-0689-z