ethyl 2,5-dihydro-2,5-dioxopyrano[3,2-c]chromene-4-carboxylate | 1225049-46-6

• 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: ethyl 2,5-dihydro-2,5-dioxopyrano[3,2-c]chromene-4-carboxylate
• 英文别名: ethyl 2,5-dioxo-2,5-dihydropyrano[3,2-c]chromene-4-carboxylate
• CAS: 1225049-46-6
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: VNFAPVCDYZQBMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.72
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 丁炔二酸二乙酯 在 copper(II) oxide 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 以95%的产率得到ethyl 2,5-dihydro-2,5-dioxopyrano[3,2-c]chromene-4-carboxylate
  参考文献：
  名称：

  Copper oxide catalyzed domino process for the synthesis of substituted 2H-pyran-2-ones and polyhydroxy coumarin derivatives

  摘要：

  DOI：

  10.1016/j.tet.2014.07.032

文献信息

• Nano Clinoptilolite: Highly Efficient Catalyst for the Synthesis of Chromene Derivatives Under Solvent-Free Conditions
  作者：Sara Hallajian、Mohammad Khalilzadeh、Mahgol Tajbakhsh、Eskandar Alipour、Zahra Safaei

  DOI：10.2174/1386207318666150424104452

  日期：2015.7.22

  An efficient and selective synthesis of substituted chromene derivatives via three-component reaction of 4-hydroxycoumarin or 1,3-dicarbonyl compounds, activated acetylenic compounds and N-nucleophiles is described. The reaction was conducted under solvent-free conditions at 70°C using potassium fluoride impregnated on natural zeolite as a cheap and available solid base. The procedure has several advantages

  描述了通过4-羟基香豆素或1，3-二羰基化合物，活化的炔属化合物和N-亲核试剂的三组分反应有效且选择性地合成取代的色烯衍生物。该反应在70℃无溶剂条件下进行，使用氟化钾浸渍在天然沸石上作为廉价和可获得的固体碱。该方法具有多个优点，包括选择性，优异的产率和方便的后处理方法。
• Expeditious Solvent-Free Synthesis of Chromene Derivatives via Three- Component Reactions of N-Nucleophiles
  作者：Mohammad R. Hosseini-Tabatabaei、Faramarz Rostami-Charati

  DOI：10.2174/138620712803901126

  日期：2012.11.7

  Multicomponent reactions involving 4-hydroxycumarine, activated acetylenic compounds and N-nucleophiles under solvent-free conditions were investigated. The reactions could also be extended to quinoline or CH-acides. Substituted chromen could be obtained from this routine, which may have potential applications in drugs fields.

  研究了在无溶剂条件下涉及4-羟基枯草碱，活化的炔类化合物和N-亲核试剂的多组分反应。反应也可以扩展至喹啉或CH-酸。可以从该例行程序中获得取代的铬烯，它可能在药物领域具有潜在的应用。
• Isoquinoline-catalyzed reaction between 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one and dialkyl acetylene dicarboxylates: synthesis of coumarin and pyranopyrane derivatives
  作者：Mohammad Anary-Abbasinejad、Hossein Anaraki-Ardakani、Mohammad Hossein Mosslemin、Hamid Reza Khavasi

  DOI：10.1590/s0103-50532010000200018

  日期：——

  In this work we report the reaction between dialkyl acetylenedicarboxylates and enolic systems such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one in the presence of isoquinoline, which leads to new coumarin and pyranopyran derivatives.