7-Propan-2-yl-2-propyl-2,6,7,8-tetrahydrochromen-5-one | 504439-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Propan-2-yl-2-propyl-2,6,7,8-tetrahydrochromen-5-one
• CAS: 504439-20-7
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: PJYQDSWBGXMXKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 7-Propan-2-yl-2-propyl-2,6,7,8-tetrahydrochromen-5-one 以 甲苯 为溶剂， 反应 24.0h， 以19%的产率得到7-Isopropyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes

  摘要：

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.

  DOI：

  10.1021/jo020688t
• 作为产物：
  描述：

  2-已烯醛 、 5-异丙基-1,3-环己二酮 在 哌啶 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到7-Propan-2-yl-2-propyl-2,6,7,8-tetrahydrochromen-5-one
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes

  摘要：

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.

  DOI：

  10.1021/jo020688t