6-methyl-4-octyl-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-methyl-4-octyl-2-pyrone
• 英文别名: 6-Methyl-4-octylpyran-2-one
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: PHBVZSWTIYRPBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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 N-甲基吡咯烷酮 、 三乙胺 、 iron(II) chloride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 6-methyl-4-octyl-2-pyrone
  参考文献：
  名称：

  铁催化的链烯基乙酸酯的交叉偶联

  摘要：

  稳定的CO键通常在交叉偶联反应中没有反应性，而交叉偶联反应通常使用更多的亲电子卤化物或活化的酯（三氟甲磺酸酯，甲苯磺酸酯）。乙酸盐价格便宜，易于获得亲电试剂，但由于其强大的CO键和极高的参与不希望的乙酰化和去质子化的能力，因此并未用于交叉偶联中。本文报道了多种乙酸烯基酯的选择性铁催化交叉偶联，它在温和的反应条件下（0°C，2 h）与不含配体的催化剂（1-2 mol％）一起运行。

  DOI：

  10.1002/anie.201504524

文献信息

• 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.
• 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.