7-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-5-one | 220633-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-5-one
• 英文别名: 7-(3,4-Dimethoxyphenyl)-2,2-dimethylpyrano[4,3-b]pyran-5-one
• CAS: 220633-48-7
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: SOTYRFANEXTISH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  间氯过氧苯甲酸 、 7-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-5-one 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到[7-(3,4-dimethoxyphenyl)-3-hydroxy-2,2-dimethyl-5-oxo-3,4-dihydropyrano[3,2-c]pyran-4-yl] 3-chlorobenzoate
  参考文献：
  名称：

  Stereoselective trans- and cis-Dihydroxylations of 2H-Pyranyl and Dihydropyridinyl Heterocycles Synthesized from Formal [3 + 3]-Cycloaddition Reactions of α,β-Unsaturated Iminium Ions with 1,3-Dicarbonyl Equivalents^†

  摘要：

  [GRAPHICS]We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones, Such difficulties led to the development of highly stereoselective trans- and cis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.

  DOI：

  10.1021/ol010034r
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 4-hydroxy-6-(3,4-dimethoxyphenyl)-2-pyrone 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以84%的产率得到7-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-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

文献信息

• Sequential 1,2-Addition−Electrocyclic Ring Closures Involving Acyclic α,β-Unsaturated Iminiums:  A Formal [3 + 3] Cycloaddition Strategy to Unique Pyranyl Spirocycles
  作者：Richard P. Hsung、Hong C. Shen、Christopher J. Douglas、Christopher D. Morgan、Shane J. Degen、Letitia J. Yao

  DOI：10.1021/jo982165k

  日期：1999.2.1
• 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
  作者：Hong C. Shen、Jiashi Wang、Kevin P. Cole、Michael J. McLaughlin、Christopher D. Morgan、Christopher J. Douglas、Richard P. Hsung、Heather A. Coverdale、Aleksey I. Gerasyuto、Juliet M. Hahn、Jia Liu、Heather M. Sklenicka、Lin-Li Wei、Luke R. Zehnder、Craig A. Zificsak

  DOI：10.1021/jo020688t

  日期：2003.3.1

  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.
• Stereoselective <i>trans-</i> and <i>cis-</i>Dihydroxylations of 2<i>H</i>-Pyranyl and Dihydropyridinyl Heterocycles Synthesized from Formal [3 + 3]-Cycloaddition Reactions of α,β-Unsaturated Iminium Ions with 1,3-Dicarbonyl Equivalents^†
  作者：Luke R. Zehnder、Lin-Li Wei、Richard P. Hsung、Kevin P. Cole、Michael J. McLaughlin、Hong C. Shen、Heather M. Sklenicka、Jiashi Wang、Craig A. Zificsak

  DOI：10.1021/ol010034r

  日期：2001.7.1

  [GRAPHICS]We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones, Such difficulties led to the development of highly stereoselective trans- and cis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.