6-isobutyl-4-methyl-2H-pyran-2-one | 30123-69-4

• 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-isobutyl-4-methyl-2H-pyran-2-one
• 英文别名: 4-Methyl-6-isobutyl-2-pyranone；4-methyl-6-(2-methylpropyl)pyran-2-one
• CAS: 30123-69-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: UGRSXCWBFBZVEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 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-isobutyl-4-methyl-2H-pyran-2-one 在 吡啶 、 tetraphosphorus decasulfide 、 盐酸羟胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-hydroxy-6-isobutyl-4-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Development of Novel N-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.9b01338
• 作为产物：
  描述：

  3,4-Epoxy-6-methyl-2-heptanon 在 硫酸 、 sodium hydride 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 61.0h， 生成 6-isobutyl-4-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Bardili, Burkhart; Marschall-Weyerstahl, Helga; Weyerstahl, Peter, Liebigs Annalen der Chemie, 1985, # 2, p. 275 - 300

  摘要：

  DOI：

文献信息

• Antifungal Activity of 4-Methyl-6-alkyl-2H-pyran-2-ones
  作者：Tarun Kumar Chattapadhyay、Prem Dureja

  DOI：10.1021/jf052792s

  日期：2006.3.1

  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.
• Notes - 2-Pyrones. XXVII. 4-Methyl-6-alkyl-2-pyrones
  作者：Richard Wiley、J. Esterle

  DOI：10.1021/jo01361a605

  日期：1957.10
• 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：——
• PITTET A. O.; KLAIBER E. M., J. AGR. AND FOOD CHEM. <JAFC-AU>, 1975, 23, NO 6, 1189-1195
  作者：PITTET A. O.、 KLAIBER E. M.

  DOI：——

  日期：——
• 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：——