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.