4-甲基-6-(1-甲基乙基)-2H-吡喃-2-酮 | 50405-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-甲基-6-(1-甲基乙基)-2H-吡喃-2-酮
• 中文别名: 乙基N-(2-异丁基-4-甲基-1-羰基戊基)甘氨酸酸酯
• 英文名称: 6-isopropyl-4-methyl-2H-pyran-2-one
• 英文别名: 4-Methyl-6-(1-methylethyl)-2H-pyran-2-on；2H-Pyran-2-one, 4-methyl-6-(1-methylethyl)-；4-methyl-6-propan-2-ylpyran-2-one
• CAS: 50405-95-3
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: YYWNAZJLTICGGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  124 °C(Press: 8 Torr)
• 密度：
  1.023±0.06 g/cm3(Predicted)
• LogP：
  1.048 (est)
• 保留指数：
  1862

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  4-甲基-6-(1-甲基乙基)-2H-吡喃-2-酮 生成 6-Isopropyl-4-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  PITTET A. O.; KLAIBER E. M., J. AGR. AND FOOD CHEM. , 1975, 23, NO 6, 1189-1195

  摘要：

  DOI：
• 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 4-甲基-6-(1-甲基乙基)-2H-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。
• Bardili, Burkhart; Marschall-Weyerstahl, Helga; Weyerstahl, Peter, Liebigs Annalen der Chemie, 1985, # 2, p. 275 - 300
  作者：Bardili, Burkhart、Marschall-Weyerstahl, Helga、Weyerstahl, Peter

  DOI：——

  日期：——
• BARDILI, B.;MARSCHALL-WEYERSTAHL, H.;WEYERSTAHL, P., LIEBIGS ANN. CHEM., 1985, N 2, 275-300
  作者：BARDILI, B.、MARSCHALL-WEYERSTAHL, H.、WEYERSTAHL, P.

  DOI：——

  日期：——
• US3972888A
  申请人：——

  公开号：US3972888A

  公开（公告）日：1976-08-03