6-(bromomethyl)-4-methyl-2-pyrone

• 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-(bromomethyl)-4-methyl-2-pyrone
• 英文别名: 6-(bromomethyl)-4-methyl-2H-pyran-2-one；6-(Bromomethyl)-4-methylpyran-2-one
• 化学式: C₇H₇BrO₂
• 分子量: 203.035
• InChiKey: SAJOCRMJOKHZMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-(bromomethyl)-4-methyl-2-pyrone 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tetraphosphorus decasulfide 、 盐酸羟胺 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 24.0h， 生成 1-羟基-4-甲基-6-(苯甲基)-2-(1H)吡啶酮
  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-(bromomethyl)-4-methyl-2-pyrone
  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

• Unexpected and efficient photochemical rearrangement of 6-hydroxyethylpyran-2-ones to 4-AIkylidene-5,6-dihydropyrans
  作者：Charles E. Chase、Michael B. Jarstfer、Atta M. Arif、F.G. West

  DOI：10.1016/0040-4039(95)01828-6

  日期：1995.11

  pendant alcohols underwent conversion to dihydropyrans 7 via irradiation in MeOH followed by stirring in the presence of catalytic HCl. This process requires the intervention of a prior skeletal rearrangement of the starting pyran-2-ones to place the hydroxyalkyl substituent at C-4, along with temporary incorporation of MeOH. Homologous substrates 2f–g underwent intramolecular 1,6-addition exclusively

  通过在MeOH中辐照，然后在有催化HCl的情况下进行搅拌，使带有Pyran-2-ones 2a-e的侧链醇转化为二氢吡喃7。此过程需要干预先进行吡喃-2-酮的骨架重排，以将羟烷基取代基置于C-4处，以及暂时掺入MeOH。同源底物2f-g仅进行分子内1,6-加成，以提供高产率的螺内酯9。
• Intramolecular [4+4]-photocycloadditions of 2-pyrones: an efficient approach to cyclooctanoid construction
  作者：F. G. West、C. E. Chase、Atta M. Arif

  DOI：10.1021/jo00067a006

  日期：1993.7

  2-Pyrones 2 bearing pendant furans underwent efficient intramolecular crossed [4 + 4]-cycloaddition to give fused bicyclic cyclooctadienes 3 and 4 bridged by lactones and ethers, along with varying amounts of [2 + 2]-adducts 5.
• 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.