6-丁基-4-甲基吡喃-2-酮 | 55510-46-8

• 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-丁基-4-甲基吡喃-2-酮
• 英文名称: 6-n-butyl-4-methyl-2H-pyran-2-one
• 英文别名: 2H-Pyran-2-one, 6-butyl-4-methyl-；6-butyl-4-methylpyran-2-one
• CAS: 55510-46-8
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JRVRVGPJKXJKLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-丁基-4-甲基吡喃-2-酮 在 四氯化碳 、 溴 作用下， 生成 2-bromo-5-hydroxy-3-methyl-nona-2c,4t-dienoic acid-lactone
  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-丁基-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

• Synthesis of .alpha.-pyrones from vinylogous thiol esters and .alpha.-oxo ketene dithioacetals
  作者：R. Karl Dieter、Jeffrey R. Fishpaugh

  DOI：10.1021/jo00244a035

  日期：1988.4
• 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.
• SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives
  作者：Kohei Sekine、Yuta Sadamitsu、Tohru Yamada

  DOI：10.1021/acs.orglett.5b03023

  日期：2015.11.20

  C-C bond forming carboxylation, and cyclization: of trimethyl(2-rnethylenbut-3,7yl)silaile derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the:corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2:furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig-cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
• 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
• DIETER, R. KARL;FISHPAUGH, JEFFREY R., J. ORG. CHEM., 53,(1988) N 9, 2031-2046
  作者：DIETER, R. KARL、FISHPAUGH, JEFFREY R.

  DOI：——

  日期：——