4-乙炔基-6-甲基-2H-吡喃-2-酮 | 502624-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-乙炔基-6-甲基-2H-吡喃-2-酮
• 英文名称: 4-ethynyl-6-methyl-2-pyrone
• 英文别名: 2H-Pyran-2-one, 4-ethynyl-6-methyl-(9CI)；4-ethynyl-6-methylpyran-2-one
• CAS: 502624-27-3
• 化学式: C₈H₆O₂
• 分子量: 134.134
• InChiKey: YOYXVALSFJOPNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  甲醇 、 4-乙炔基-6-甲基-2H-吡喃-2-酮 反应 0.5h， 以50%的产率得到methyl (E)-3-ethynyl-5-oxohex-2-enoate
  参考文献：
  名称：

  α-吡喃酮和嘧啶酮作为基于亲和力的蛋白质谱分析的光亲和探针的评价

  摘要：

  α-吡喃酮和嘧啶酮是天然产物和生物活性化合物中常见的结构基序。它们还显示出产生高能中间体的光化学，该中间体可能具有蛋白质反应性。合成了吡喃酮和嘧啶酮的文库，并评估了它们在几种粗细胞裂解物中用作基于非定向亲和力的蛋白质谱分析的光亲和探针的潜力。进一步的“原理证明”实验表明，适当支架上的嘧啶酮标签具有与二苯甲酮同样的蛋白质组标记能力。

  DOI：

  10.1021/jo201281c
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 在 copper(l) iodide 、 palladium on activated charcoal 、 四丁基氟化铵 、 三溴化磷 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-乙炔基-6-甲基-2H-吡喃-2-酮
  参考文献：
  名称：

  α-吡喃酮和嘧啶酮作为基于亲和力的蛋白质谱分析的光亲和探针的评价

  摘要：

  α-吡喃酮和嘧啶酮是天然产物和生物活性化合物中常见的结构基序。它们还显示出产生高能中间体的光化学，该中间体可能具有蛋白质反应性。合成了吡喃酮和嘧啶酮的文库，并评估了它们在几种粗细胞裂解物中用作基于非定向亲和力的蛋白质谱分析的光亲和探针的潜力。进一步的“原理证明”实验表明，适当支架上的嘧啶酮标签具有与二苯甲酮同样的蛋白质组标记能力。

  DOI：

  10.1021/jo201281c

文献信息

• Regiochemistry in Cobalt-Mediated Intermolecular Pauson–Khand Reactions of Unsymmetrical Internal Heteroaromatic Alkynes with Norbornene
  作者：Benjamin E. Moulton、Adrian C. Whitwood、Anne K. Duhme-Klair、Jason M. Lynam、Ian J. S. Fairlamb

  DOI：10.1021/jo200664m

  日期：2011.7.1

  comparable (2-phenylethynyl)heteroaromatic compounds with norbornene, mediated by Co2(CO)8 to give cyclopentenone products, were examined in this study. A synthetic protocol utilizing focused-microwave dielectric heating proved indispensable in the efficient synthesis of the PK cyclopentenone products. “π-Deficient” heteroaromatic substrates, e.g., 2-pyrones, and some “π-excessive” heteroaromatics such as

  Co 2（CO）8介导的空间可比的（2-苯基乙炔基）杂芳族化合物与降冰片烯的分子间Pauson-Khand（PK）反应得到环戊烯酮产品，在这项研究中进行了检查。事实证明，利用聚焦微波介电加热的合成协议是有效合成PK环戊烯酮产品必不可少的。“π缺陷”杂芳族底物（例如2-吡喃酮）和一些“π过量”杂芳族化合物（例如2-和3-噻吩和2-呋喃）有利于新形成的环戊烯酮环中的β位置。其他π过量的杂芳族化合物（例如2-吡咯或2-吲哚）偏向α位。π-过量的3-吲哚衍生物给出了几乎相等的区域异构体混合物。氮在含吡啶基炔烃底物中的位置也影响PK反应的区域化学结果。拥有近端氮原子的2-吡啶基炔烃相对于4-吡啶基变异体会极大地影响区域选择性，有利于新形成的环戊烯酮环中的β位置。2-嘧啶炔基表现出与2-吡啶炔基相似的行为。不参与与降冰片烯进行PK反应的化合物包括（2-苯基乙炔基）咪唑和相关的苯并咪唑类，它们可促进原位生成的快速分解（μ2-炔）Co
• An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone
  作者：Lester R. Marrison、Julia M. Dickinson、Razwan Ahmed、Ian J.S. Fairlamb

  DOI：10.1016/s0040-4039(02)02207-4

  日期：2002.12

  We herein report the efficient syntheses of biologically active 4-alkenyl- and 4-alkynyl-6-methyl-2-pyrones using Pd-catalysed coupling procedures. A palladium on carbon/triphenylphosphine combination is shown to be the most effective catalyst for Sonogashira cross-coupling of several terminal acetylenes with 4-bromo-6-methyl-2-pyrone in yields of up to 95%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.