6-n-heptyl-4-methyl-2H-pyran-2-one | 50405-90-8

• 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-n-heptyl-4-methyl-2H-pyran-2-one
• 英文别名: 6-heptyl-4-methyl-2H-pyran-2-one；6-n-heptyl-4-methyl-α-pyrone；6-Heptyl-4-methylpyran-2-one
• CAS: 50405-90-8
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: NZOIQQPLYQYQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-n-heptyl-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 6-heptyl-1-hydroxy-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：

  3,3-二甲基丙烯酸甲酯 在 aluminum (III) chloride 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 6-n-heptyl-4-methyl-2H-pyran-2-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

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。
• 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.
• Lohaus; Dittmar, Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 8 a, p. 1311 - 1316
  作者：Lohaus、Dittmar

  DOI：——

  日期：——
• US3972888A
  申请人：——

  公开号：US3972888A

  公开（公告）日：1976-08-03
• 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.