4-ethyl-6-methyl-2-pyrone | 106319-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-ethyl-6-methyl-2-pyrone
• 英文别名: 4-ethyl-6-methyl-2H-pyran-2-one；4-Ethyl-6-methylpyran-2-one
• CAS: 106319-13-5
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: GNKVBPVDICORFY-UHFFFAOYSA-N

物化性质

• 沸点：
  250.6±9.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 thalium carbonate 、 三溴化磷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-ethyl-6-methyl-2-pyrone
  参考文献：
  名称：

  Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines

  摘要：

  Bioactive synthetic 4-substituted-6-methyl-2-pyrones are reported. Various 4-substitutents have been incorporated using Pd-catalysed carbon-carbon bond coupling procedures. Preliminary screening of the 2-pyrones against human ovarian carcinoma (A2780) and human chronic myelogenous leukaemia (K562) cell lines show that 4-alkynyl-6-methyl-2-pyrones have excellent potential as anticancer agents. The pyrones demonstrate broad spectrum antimicrobial activities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00824-7

文献信息

• 2-Pyrones possessing antimicrobial and cytotoxic activities
  作者：Ian J.S Fairlamb、Lester R Marrison、Julia M Dickinson、Feng-Ju Lu、Jan Peter Schmidt

  DOI：10.1016/j.bmc.2004.01.051

  日期：2004.8.1

  The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile-base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.
• Regioselective alkylations of 4,6-dialkyl substituted 2(H)-pyran-2-ones
  作者：R. Karl Dieter、Jeffrey R. Fishpaugh

  DOI：10.1021/jo00381a037

  日期：1987.3
• DIETER R. K.; FISHPAUGH J. R., J. ORG. CHEM., 52,(1987) N 5, 523-526
  作者：DIETER R. K.、 FISHPAUGH J. R.

  DOI：——

  日期：——
• Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines
  作者：Lester R. Marrison、Julia M. Dickinson、Ian J.S. Fairlamb

  DOI：10.1016/s0960-894x(02)00824-7

  日期：2002.12

  Bioactive synthetic 4-substituted-6-methyl-2-pyrones are reported. Various 4-substitutents have been incorporated using Pd-catalysed carbon-carbon bond coupling procedures. Preliminary screening of the 2-pyrones against human ovarian carcinoma (A2780) and human chronic myelogenous leukaemia (K562) cell lines show that 4-alkynyl-6-methyl-2-pyrones have excellent potential as anticancer agents. The pyrones demonstrate broad spectrum antimicrobial activities. (C) 2002 Elsevier Science Ltd. All rights reserved.