6-乙基-4-甲基-吡喃-2-酮 | 17422-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-乙基-4-甲基-吡喃-2-酮
• 英文名称: 6-ethyl-4-methyl-2H-pyran-2-one
• 英文别名: 6-ethyl-4-methylpyran-2-one
• CAS: 17422-71-8
• 化学式: C₈H₁₀O₂
• mdl: MFCD09033707
• 分子量: 138.166
• InChiKey: OOJGOOZLZPDSGU-UHFFFAOYSA-N

物化性质

• 沸点：
  100-115 °C(Press: 4 Torr)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-乙基-4-甲基-吡喃-2-酮 在 四氯化碳 、 溴 作用下， 生成 2-bromo-5-hydroxy-3-methyl-hepta-2c,4t-dienoic acid-lactone
  参考文献：
  名称：

  Preparation and Decarboxylation of C-Acylated β-Methylglutaconic Anhydrides¹

  摘要：

  DOI：

  10.1021/ja01135a054
• 作为产物：
  描述：

  3,3-二甲基丙烯酸甲酯 在 三氯化铝 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 6-乙基-4-甲基-吡喃-2-酮
  参考文献：
  名称：

  Antifungal Activity of 4-Methyl-6-alkyl-2H-pyran-2-ones

  摘要：

  A number of 4-methyl-6-alkyl-alpha-pyrones were synthesized and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-alpha-pyrone, 4-methyl-6-pentyl-alpha-pyrone, 4-methyl-6-hexyl-alpha-pyrone, and 4-methyl-6-heptyl-alpha-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 mu g/mL. 4-Methyl-6-hexyl-alpha-pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-alpha-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.

  DOI：

  10.1021/jf052792s

文献信息

• Formal Ring-Opening/Cross-Coupling Reactions of 2-Pyrones: Iron-Catalyzed Entry into Stereodefined Dienyl Carboxylates
  作者：Chang-Liang Sun、Alois Fürstner

  DOI：10.1002/anie.201307028

  日期：2013.12.2

  exceptional level of sophistication in cross‐coupling chemistry, reactions of substrates that incorporate the leaving group as an integral part into a heterocyclic scaffold are scarce. The title reaction outlines the utility of this reaction format (see scheme; acac=acetylacetonate), provides a convenient entry into stereodefined diene carboxylates, and adds a new chapter to the field of iron catalysis.

  开放获取：尽管交叉偶联化学的复杂程度非常高，但将离去基团作为整体组成部分整合到杂环支架中的底物的反应却很少。标题反应概述了该反应形式的用途（参见方案； acac =乙酰丙酮化物），为立体定义的二烯羧酸盐的合成提供了便利，并为铁催化领域增添了新篇章。
• Iron‐Catalyzed Reactions of 2‐Pyridone Derivatives: 1,6‐Addition and Formal Ring Opening/Cross Coupling
  作者：Lin Huang、Yiting Gu、Alois Fürstner

  DOI：10.1002/asia.201900865

  日期：2019.11.18

  In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives

  在简单的铁盐存在下，2-吡啶酮衍生物在温和的条件下与格氏试剂反应，生成相应的1,6-加成产物。如果在实际添加步骤之后向反应介质中添加了质子惰性的偶极助溶剂，则中间体主要形成屈服开环，从而导致非热力学的Z，E构型的二烯酰胺衍生物，否则很难制备。对照实验以及（三羰基）铁吡啶酮配合物的分离和晶体学表征表明，原位生成的活性铁催化剂对嵌入基质杂环系统中的极化二烯系统表现出高亲和力，这很可能是因为实际识别元素。
• Palladium-catalysed annulation reaction of allenyltins with β-iodo vinylic acids: selective synthesis of α-pyrones
  作者：Séverine Rousset、Mohamed Abarbri、Jérôme Thibonnet、Alain Duchêne、Jean-Luc Parrain

  DOI：10.1039/b005886f

  日期：——

  Palladium-catalysed regio- and stereoselective annulation of allenyl stannanes by β-iodo vinylic acids gives the corresponding α-pyrones in high yields. This annulation most probably proceeds through a Stille reaction/cyclisation sequence.

  钯催化的 β-碘乙烯酸对丙二烯基锡烷进行区域选择性和立体选择性环化，以高产率得到相应的 α-吡喃酮。这种环化很可能通过 Stille 反应/环化序列进行。
• Synthesis of Isocoumarins and α-Pyrones via Tandem Stille Reaction/Heterocyclization
  作者：Khalil Cherry、Jean-Luc Parrain、Jérôme Thibonnet、Alain Duchêne、Mohamed Abarbri

  DOI：10.1021/jo050638z

  日期：2005.8.1

  A general route to α-pyrones and 3-substituted isocoumarins from (Z)-iodovinylic acids 1a−f or 2-iodobenzoic acids 4a−c is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic acids 1a−f or 2-iodobenzoic acids 4a−c with various allenyltributyltin reagents in the presence of palladium acetate, triphenylphosphine, and tetrabutylammonium bromide in

  描述了从（Z）-碘乙烯基酸1a - f或2-碘苯甲酸4a - c制备α-吡喃酮和3-取代的异香豆素的一般途径，包括在芳环上带有取代基的化合物。的治疗（ż）-β-iodovinylic酸1A - ˚F或2-碘酸4A - Ç在乙酸钯，三苯基膦，和存在与各种试剂allenyltributyltin四丁基溴化铵在二甲基甲酰胺中提供的相应的α吡喃酮的良好的产率3A - ķ或3-取代的异香豆素5A -克经由串联Stille反应和6-内切-Dig oxacyclization。
• Regioselective alkylations of 4,6-dialkyl substituted 2(H)-pyran-2-ones
  作者：R. Karl Dieter、Jeffrey R. Fishpaugh

  DOI：10.1021/jo00381a037

  日期：1987.3