4-甲基-6-戊基-2H-吡喃-2-酮 | 55510-47-9

• 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-戊基-2H-吡喃-2-酮
• 英文名称: 4-methyl-6-n-pentyl-2H-pyran-2-one
• 英文别名: 4-methyl-6-pentyl-2H-pyran-2-one；4-methyl-6-n-pentyl-α-pyrone；4-methyl-6-pentyl-pyran-2-one；5-hydroxy-3-methyl-deca-2c,4t-dienoic acid-lactone；5-Hydroxy-3-methyl-deca-2c,4t-diensaeure-lacton；2H-Pyran-2-one, 4-methyl-6-pentyl-；4-methyl-6-pentylpyran-2-one
• CAS: 55510-47-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: GBYBTBXDHBXDMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  103 °C(Press: 1 Torr)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-甲基-6-戊基-2H-吡喃-2-酮 生成 4-甲基-6-戊基四氢-2H-吡喃-2-酮
  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-戊基-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

• Syntheses of α-Pyrones Using Gold-Catalyzed Coupling Reactions
  作者：Tuoping Luo、Mingji Dai、Shao-Liang Zheng、Stuart L. Schreiber

  DOI：10.1021/ol200794w

  日期：2011.6.3

  Sequential alkyne activation of terminal alkynes and propiolic acids by gold(I) catalysts yields compounds having α-pyrone skeletons. Novel cascade reactions involving propiolic acids are reported that give rise to α-pyrones with different substitution patterns.

  通过金 (I) 催化剂对末端炔烃和丙炔酸进行顺序炔烃活化产生具有 α-吡喃酮骨架的化合物。据报道，涉及丙炔酸的新型级联反应会产生具有不同取代模式的 α-吡喃酮。
• Smoking composition containing a vanillin-release additive
  申请人：Philip Morris Products Inc.

  公开号：EP0470766A2

  公开（公告）日：1992-02-12

  This invention provides smoking compositions which contain a novel vanillyl 5-hydroxyester flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as 4′-formyl-2′-methoxyphenyl 5-hydroxy-2-isopropylhexanoate pyrolyzes into vanillin and 2-isopropyl-5-hydroxyhexanoic acid delta lactone flavorants as volatile components of the cigarette smoke.

  本发明提供了含有新型香草醇 5-羟基酯香料释放添加剂的烟用组合物。 在卷烟吸食条件下，可燃填料和/或包装纸添加剂（如 4′-甲酰基-2′-甲氧基苯基 5-羟基-2-异丙基己酸酯）会热解成香兰素和 2-异丙基-5-羟基己酸δ内酯香料，作为卷烟烟气中的挥发性成分。
• 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.
• Development of Novel <i>N</i>-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents
  作者：Linghao Hu、Hongxuan Feng、Hongguang Zhang、Songda Yu、Qinyuan Zhao、Wei Wang、Fengxia Bao、Xun Ding、Jiajing Hu、Manjiong Wang、Yixiang Xu、Zengrui Wu、Xiaokang Li、Yun Tang、Fei Mao、Xiaoyan Chen、Haiyan Zhang、Jian Li

  DOI：10.1021/acs.jmedchem.9b01338

  日期：2020.2.13

  Our previous study had identified ciclopirox (CPX) as a promising lead compound for treatment of ischemic stroke. To find better neuroprotective agents, a series of N-hydroxypyridone derivatives based on CPX were designed, synthesized, and evaluated in this study. Among these derivatives, compound 11 exhibits significant neuroprotection against oxygen glucose deprivation and oxidative stress -induced injuries in neuronal cells. Moreover, compound 11 possesses good blood-brain barrier permeability and superior antioxidant capability. In addition, a complex of compound 11 with olamine-11.01a possesses good water solubility, negligible hERG inhibition, and superior metabolic stability. The in vivo experiment demonstrates that 11.01a significantly reduces brain infarction and alleviates neurological deficits in middle cerebral artery occlusion rats. Hence, compound 11.01a is identified in our research as a prospective prototype in the innovation of stroke treatment.
• Notes - 2-Pyrones. XXVII. 4-Methyl-6-alkyl-2-pyrones
  作者：Richard Wiley、J. Esterle

  DOI：10.1021/jo01361a605

  日期：1957.10