6-butyl-4-methyl-5,6-dihydro-2H-pyran-2-one | 99181-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-butyl-4-methyl-5,6-dihydro-2H-pyran-2-one
• 英文别名: (+/-)-5-hydroxy-3-methyl-non-2c-enoic acid-lactone；(+/-)-5-Hydroxy-3-methyl-non-2c-ensaeure-lacton；2-Butyl-4-methyl-2,3-dihydropyran-6-one
• CAS: 99181-35-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: YEJUZABRRUOEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,6-二甲基-2-氧-2H-吡喃-5-甲酸乙酯 在 氢氧化钾 、 2,4-二甲基吡啶 、 copper diacetate 作用下， 生成 6-butyl-4-methyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  2-Pyrones. XXVI. Alkylidene Methylglutaconic Acids and 3,6-Dialkyl-5-carboxy-5,6-dihydro-2-pyrones from Methyl β-Methylglutaconate and Ethyl Isodehydroacetate and their Isomerization and Decarboxylation

  摘要：

  DOI：

  10.1021/ja01566a067

文献信息

• Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor
  作者：Andrea D'Annibale、Laura Ciaralli、Mauro Bassetti、Chiara Pasquini

  DOI：10.1021/jo070600h

  日期：2007.8.1

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.
• 2-Pyrones. XXVI. Alkylidene Methylglutaconic Acids and 3,6-Dialkyl-5-carboxy-5,6-dihydro-2-pyrones from Methyl β-Methylglutaconate and Ethyl Isodehydroacetate and their Isomerization and Decarboxylation
  作者：Richard H. Wiley、H. G. Ellert

  DOI：10.1021/ja01566a067

  日期：1957.5