3,3,5,5-tetramethyl-6-(propan-2-ylidene)-dihydro-3H-pyran-2,4-dione | 10319-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,3,5,5-tetramethyl-6-(propan-2-ylidene)-dihydro-3H-pyran-2,4-dione
• 英文别名: 5-Hydroxy-2,2,4,4,6-pentamethylen-3-oxo-hept-5-en-saeure-δ-lacton；5-Hydroxy-2,2,4,4,6-pentamethyl-3-oxo-hept-5-en-saeure-δ-lacton；3,3,5,5-tetramethyl-6-propan-2-ylideneoxane-2,4-dione
• CAS: 10319-92-3
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: IIWYYTCARSNFEX-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±35.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3,5,5-tetramethyl-6-(propan-2-ylidene)-dihydro-3H-pyran-2,4-dione 在 ammonium hydroxide 作用下， 生成 2.2.4.4.6-Pentamethyl-3.5-dioxo-heptansaeure-amid
  参考文献：
  名称：

  Lactone trimer of dimethylketene

  摘要：

  DOI：

  10.1021/jo01288a031
• 作为产物：
  描述：

  四甲基环丁烷-1,3-二酮 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以76%的产率得到六甲基环己烷-1,3,5-三酮
  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