3-<3-(2'-Furyl)propyl>-2,5,6-trimethyl-4H-pyran-4-one | 151831-63-9

• 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>-2,5,6-trimethyl-4H-pyran-4-one
• 英文别名: 3-[3-(Furan-2-yl)propyl]-2,5,6-trimethylpyran-4-one
• CAS: 151831-63-9
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: STIOOOYJFZSALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<3-(2'-Furyl)propyl>-2,5,6-trimethyl-4H-pyran-4-one 以 various solvent(s) 为溶剂， 反应 2.0h， 以17%的产率得到(1R,5S,8R,9S,10S,12R)-9,10,12-trimethyl-11,14-dioxapentacyclo[7.3.1.15,8.01,5.010,12]tetradec-6-en-13-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
• 作为产物：
  描述：

  2,3,5,6-Tetramethyl-4H-pyran-4-one 在 四丁基硫酸氢铵 、 过氧化苯甲酰 sodium hydroxide 、 sodium dihydrogenphosphate 、 sodium amalgam 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-<3-(2'-Furyl)propyl>-2,5,6-trimethyl-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

• 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.