3-<<3-(2'-Furyl)propyl>oxy>-2-methyl-4H-pyran-4-one | 151831-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-<<3-(2'-Furyl)propyl>oxy>-2-methyl-4H-pyran-4-one
• 英文别名: 3-[3-(Furan-2-yl)propoxy]-2-methylpyran-4-one
• CAS: 151831-70-8
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: XVENUPUFRHYUFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙醇 、 3-<<3-(2'-Furyl)propyl>oxy>-2-methyl-4H-pyran-4-one 反应 2.0h， 以58%的产率得到
  参考文献：
  名称：

  Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons

  摘要：

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.

  DOI：

  10.1021/jo00076a047
• 作为产物：
  描述：

  furnish 2-(3-bromopropyl)furan 、 麦芽醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以52%的产率得到3-<<3-(2'-Furyl)propyl>oxy>-2-methyl-4H-pyran-4-one
  参考文献：
  名称：

  Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons

  摘要：

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.

  DOI：

  10.1021/jo00076a047

文献信息

• Novel bicyclic oxazolines via nitrile capture of photochemically generated oxyallyl zwitterions
  作者：F. G. West、Daniel J. Koch

  DOI：10.1039/c39930001681

  日期：——

  Several 4-pyrones bearing 3-alkoxy substituents have been photolysed in acetonitrile to give in two cases novel bicyclic oxazolines, arising from apparent Ritter-type capture of the intermediate oxyallyl zwitterion followed by intramolecular nitrilium trapping by alkoxide.

  几种带有3-烷氧基取代基的4-吡喃酮在乙腈中发生光解，在两种情况下产生了新的双环恶唑啉，这是由于中间体氧代烯丙基两性离子发生了明显的Ritter型捕获，随后被烷氧基分子内腈捕获。
• Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons
  作者：F. G. West、Claudia Hartke-Karger、Daniel J. Koch、Cynthia E. Kuehn、A. M. Arif

  DOI：10.1021/jo00076a047

  日期：1993.11

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.