5-[(4-Methoxyphenyl)methoxy]-2-(prop-2-enoxymethyl)pyran-4-one | 181647-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[(4-Methoxyphenyl)methoxy]-2-(prop-2-enoxymethyl)pyran-4-one
• CAS: 181647-72-3
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: AATFSPJEYCVWEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  5-[(4-Methoxyphenyl)methoxy]-2-(prop-2-enoxymethyl)pyran-4-one 在 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-Hydroxy-1-methyl-2-(prop-2-enoxymethyl)pyridin-4-one
  参考文献：
  名称：

  3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo[3.2.1]octanes

  摘要：

  3-Hydroxy-4-pyridones, which are easily prepared from commercially available 3-hydroxy-4-pyrones, can be readily transformed into 4-methoxy-3-oxidopyridinium ylides by treatment with methyl trifluoromethanesulfonate and subsequent deprotonation with a non-nucleophilic base. These ylides are capable of undergoing cycloaddition to several electron-deficient alkenes, thus allowing the synthesis of highly functionalized azabicyclo[3.2,1]octane moieties. The rich substitution patterns of these frameworks might allow their divergent conversion to a variety of natural and non-natural tropane alkaloids.

  DOI：

  10.1021/jo960854v
• 作为产物：
  描述：

  曲酸 在 aluminum oxide 、 potassium fluoride 、 氢氧化钾 、 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 反应 40.0h， 生成 5-[(4-Methoxyphenyl)methoxy]-2-(prop-2-enoxymethyl)pyran-4-one
  参考文献：
  名称：

  3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo[3.2.1]octanes

  摘要：

  3-Hydroxy-4-pyridones, which are easily prepared from commercially available 3-hydroxy-4-pyrones, can be readily transformed into 4-methoxy-3-oxidopyridinium ylides by treatment with methyl trifluoromethanesulfonate and subsequent deprotonation with a non-nucleophilic base. These ylides are capable of undergoing cycloaddition to several electron-deficient alkenes, thus allowing the synthesis of highly functionalized azabicyclo[3.2,1]octane moieties. The rich substitution patterns of these frameworks might allow their divergent conversion to a variety of natural and non-natural tropane alkaloids.

  DOI：

  10.1021/jo960854v

文献信息

• Investigation of Transfer Group, Tether Proximity, and Alkene Substitution for Intramolecular Silyloxypyrone-Based [5 + 2] Cycloadditions
  作者：Jacob J. Bulandr、Jacob P. Grabowski、Chunyin M. Law、Jessica L. Shaw、John R. Goodell、T. Andrew Mitchell

  DOI：10.1021/acs.joc.9b01479

  日期：2019.8.16

  cycloadditions revealed three significant factors impacting conversion to cycloadduct: (1) the silyl transfer group has a substantial influence on the rate of reaction, and the robust t-butyldiphenylsilyl group was found to be more effective overall than the conventional t-butyldimethylsilyl group; (2) α,β-unsaturated esters were generally more reactive than terminal olefins and afforded appreciable quantity

  分子内基于甲硅烷基氧吡喃酮的[5 + 2]环加成反应的系统研究表明，影响转化为环加合物的三个重要因素：（1）甲硅烷基转移基团对反应速率有重大影响，并且发现坚固的叔丁基二苯基甲硅烷基是总体上比常规t更有效-丁基二甲基甲硅烷基；（2）α，β-不饱和酯的反应性通常比末端烯烃更高，即使在室温下也能提供相当数量的环加合物。（3）系链与甲硅烷基转移基团的接近揭示了吡喃酮与烯烃之间的临界排列趋势。综上所述，这些研究提供了有关影响这些反应的范围和局限性的空间和电子参数的见解。
• 3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo[3.2.1]octanes
  作者：Antonio Rumbo、Antonio Mouriño、Luis Castedo、José L. Mascareñas

  DOI：10.1021/jo960854v

  日期：1996.1.1

  3-Hydroxy-4-pyridones, which are easily prepared from commercially available 3-hydroxy-4-pyrones, can be readily transformed into 4-methoxy-3-oxidopyridinium ylides by treatment with methyl trifluoromethanesulfonate and subsequent deprotonation with a non-nucleophilic base. These ylides are capable of undergoing cycloaddition to several electron-deficient alkenes, thus allowing the synthesis of highly functionalized azabicyclo[3.2,1]octane moieties. The rich substitution patterns of these frameworks might allow their divergent conversion to a variety of natural and non-natural tropane alkaloids.