methyl 6-methylcoumarin-4-carboxylate | 206354-66-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: methyl 6-methylcoumarin-4-carboxylate
• 英文别名: methyl-6-methyl-2-oxo-2H-chromene-4-carboxylate；Methyl 6-methyl-2-oxo-2H-1-benzopyran-4-carboxylate；methyl 6-methyl-2-oxochromene-4-carboxylate
• CAS: 206354-66-7
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: XWPBJAICNVHWQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲酚 、 丁炔二酸二甲酯 在 1-(4-diphenylphosphinitebutyl)-3-methylimidazolium chloride 作用下， 反应 0.03h， 以76%的产率得到methyl 6-methylcoumarin-4-carboxylate
  参考文献：
  名称：

  次膦酸盐离子液体（IL-OPPh 2）作为可循环使用的试剂，可在微波辐射条件下有效合成香豆素

  摘要：

  特定于任务的次膦酸酯离子液体（IL-OPPh 2）被用作试剂，用于在微波辐射条件下通过乙炔二羧酸二（甲基或乙基）酯与酚类化合物的反应有效合成4-取代的香豆素。研究了亚膦酸酯离子液体的量，反应温度和反应时间等参数对该方法的影响。使用这种温和的一锅法在无溶剂条件下以高收率获得了产品。另外，离子液体循环测试表明它可以重复使用3次而不会损失其活性。

  DOI：

  10.1007/bf03245917

文献信息

• Synthesis of Dimethyl 2-(2,4,6-Trimethylphenoxy)-3-triphenylphosphoniobutanedioate and its Application in Intramolecular Wittig Reactions
  作者：Issa Yavari、Farahnaz Nourmohammadian、Hamid R. Bijanzadeh

  DOI：10.1080/10426500211709

  日期：2002.5.1

  Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by 2,4,6-trimethylphenol leads to a stable ylide in high yield, which is employed in intramolecular Wittig reactions.

  2,4,6-三甲基苯酚对三苯基膦和乙炔二甲酸二甲酯反应中产生的反应性 1:1 中间体进行质子化，以高产率得到稳定的叶立德，可用于分子内 Wittig 反应。
• A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt
  作者：Issa Yavari、Rahim Hekmat-Shoar、Afsaneh Zonouzi

  DOI：10.1016/s0040-4039(98)00206-8

  日期：1998.4

  Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by substituted phenols leads to a vinyltriphenylphosphonium salt, which undergoes aromatic electrophilic substitution reaction with the phenolate conjugate base to produce 4-carboxymethylcoumarins in fairly high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Novel Synthesis of Oxygenated Coumarins from Substituted Phenols Mediated by Vinyl Triphenylphosphonium Salt Under Microwave Irradiation
  作者：Rahim Hekmatshoar、Sanaz Souri、Mahshid Rahimifard、Farnoosh Faridbod

  DOI：10.1080/10426500214882

  日期：2002.12.1

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate(DMAD) by substituted phenols lead to vinyl triphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with a phenolate conjugate base to produce. 4-carboxymethyl coumarins in fairly highly yields.
• Phosphinite ionic liquid (IL-OPPh2) as a recyclable reagent for the efficient synthesis of coumarins under microwave irradiation conditions
  作者：H. Valizadeh、H. Gholipour、M. Mahmoudian

  DOI：10.1007/bf03245917

  日期：2011.9

  the efficient synthesis of 4-substituted coumarins via the reaction of di(methyl or ethyl) acetylenedicarboxylate with phenolic compounds under microwave irradiation conditions. The effects of parameters such as the amount of the phosphinite ionic liquid, reaction temperature and reaction time on this procedure were investigated. Products were obtained in good yields using this mild and one-pot methodology

  特定于任务的次膦酸酯离子液体（IL-OPPh 2）被用作试剂，用于在微波辐射条件下通过乙炔二羧酸二（甲基或乙基）酯与酚类化合物的反应有效合成4-取代的香豆素。研究了亚膦酸酯离子液体的量，反应温度和反应时间等参数对该方法的影响。使用这种温和的一锅法在无溶剂条件下以高收率获得了产品。另外，离子液体循环测试表明它可以重复使用3次而不会损失其活性。