4-(4'-acetylphenylethynyl)-6-methyl-2-pyrone | 502624-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4'-acetylphenylethynyl)-6-methyl-2-pyrone
• 英文别名: 2H-Pyran-2-one, 4-[(4-acetylphenyl)ethynyl]-6-methyl-；4-[2-(4-acetylphenyl)ethynyl]-6-methylpyran-2-one
• CAS: 502624-26-2
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: WDRTXSBNMYMWED-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  412.2±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 在 palladium on activated charcoal copper(l) iodide 、 三溴化磷 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 4-(4'-acetylphenylethynyl)-6-methyl-2-pyrone
  参考文献：
  名称：

  An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02207-4

文献信息

• Palladium-Catalysed Alkynylations of 2-Pyrone (Pyran-2-one) Halides
  作者：Ian J. Fairlamb、Feng Ju Lu、Jan Peter Schmidt

  DOI：10.1055/s-2003-42405

  日期：——

  The 2-pyrone sub-unit is found in a large number of natural products possessing broad-spectrum biological activity. As such, efficient synthetic methods are required to enable facile access to substituted 2-pyrone derivatives. Important conditions for the Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone (3a) have been developed, and compared against Negishi’s methodology. The best conditions for Sonogashira alkynylation was found to be the use of Pd/C with added Ph3P as the catalyst, in the presence of catalytic CuI, in a mixture of MeCN and Et3N at reflux. Using Negishi’s standard conditions, terminal alkynylzinc reagents, generated in situ from terminal alkynes with LDA or n-BuLi and subsequent reaction with anhydrous ZnBr2, were reacted with 3a at room temperature using Pd(PPh3)4 as the catalyst in THF.

  2-吡喃酮亚基存在于许多具有广谱生物活性的天然产物中。因此，需要高效的合成方法以便于制备取代的2-吡喃酮衍生物。已经开发出重要的条件用于4-溴-6-甲基-2-吡喃酮（3a）的Sonogashira炔基化反应，并与其基于Negishi的方法进行了比较。最佳的Sonogashira炔基化条件是使用添加了Ph3P的Pd/C作为催化剂，在含有催化量CuI的MeCN和Et3N混合物中回流。按照Negishi的标准条件，由端炔与LDA或n-BuLi反应生成并随后与无水ZnBr2反应生成的端炔基锌试剂，在室温下以Pd(PPh3)4作为催化剂在THF中与3a反应。
• 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.