6-hexyl-4-methyl-2H-pyran-2-one | 57058-19-2

• 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-hexyl-4-methyl-2H-pyran-2-one
• 英文别名: 6-n-hexyl-4-methyl-2H-pyran-2-one；6-n-hexyl-4-methyl-α-pyrone；6-hexyl-4-methyl-pyran-2-one；5-hydroxy-3-methyl-undeca-2c,4t-dienoic acid-lactone；5-Hydroxy-3-methyl-undeca-2c,4t-diensaeure-lacton；6-Hexyl-4-methylpyran-2-one
• CAS: 57058-19-2
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: SBXDFLJHTJDVBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hexyl-4-methyl-2H-pyran-2-one 在 palladium on activated charcoal 、 乙醚 作用下， 生成 6-hexyl-4-methyltetrahydropyran-2-one
  参考文献：
  名称：

  Notes - 2-Pyrones. XXVII. 4-Methyl-6-alkyl-2-pyrones

  摘要：

  DOI：

  10.1021/jo01361a605
• 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-hexyl-4-methyl-2H-pyran-2-one
  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

• Copper(I)-Catalysed Multicomponent Reaction: Straightforward Access to 5-Hydroxy-1<i>H</i>-pyrrol-2(5<i>H</i>)-ones
  作者：Muhammad Idham Darussalam Mardjan、Jean-Luc Parrain、Laurent Commeiras

  DOI：10.1002/adsc.201500994

  日期：2016.2.18

  multicomponent coupling reaction between readily available (Z)‐3‐iodoacrylic acids, terminal alkynes, and primary amines was developed to smoothly access a small library of 5‐hydroxy‐1H‐pyrrol‐2(5H)‐ones in good yields. This practical and general process was applied to a short‐steps synthesis of the natural product pulchellalactam.

  已开发出易于获得的（Z）-3-碘代丙烯酸，末端炔烃和伯胺之间的铜催化多组分偶联反应，以顺利访问5-羟基-1 H-吡咯-2（5 H）-one的小型文库丰产。该实用且通用的方法适用于天然产物普氏内酰胺的短步合成。
• 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。
• Copper-Catalyzed Preparation of γ-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions
  作者：Samuel Inack-Ngi、Raphaël Rahmani、Laurent Commeiras、Gaëlle Chouraqui、Jérôme Thibonnet、Alain Duchêne、Mohamed Abarbri、Jean-Luc Parrain

  DOI：10.1002/adsc.200800757

  日期：2009.3

  Abstractmagnified imageA general and efficient copper(I)‐catalyzed cross‐coupling and heterocyclization reaction of terminal alkynes and β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5‐ylidenebutenolides and 3‐substituted isocoumarins with excellent regio‐ and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium‐free.
• Regio- and stereoselective preparation of γ-alkylidenebutenolides or α-pyrones using a Stille reaction and palladium-catalysed oxacyclisation sequence
  作者：Séverine Rousset、Mohamed Abarbri、Jérôme Thibonnet、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1016/j.tetlet.2003.08.043

  日期：2003.10

  Synthesis of butenolides or alpha-pyrones from substituted tributylstannyl acetylides is highly dependant on the nature of the acetylide. (C) 2003 Elsevier Ltd. All rights reserved.