ethyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylate
• 英文别名: ethyl 5,6,7,8-tetrahydro-2,5-dioxo-2H-chromene-4-carboxylate；ethyl 2,5-dioxo-7,8-dihydro-6H-chromene-4-carboxylate
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: MFRPRAAGEBOHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 silica gel 作用下， 反应 0.15h， 生成 ethyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylate
  参考文献：
  名称：

  在无溶剂条件下，在硅胶粉末存在的情况下，稳定的磷叶立德通过微波诱导转化为缺电子的 2H-Cheromenes

  摘要：

  在三苯基膦和二烷基乙炔二羧酸酯之间的反应中产生的高反应性 1:1 中间体被环己 1,3-二酮质子化产生乙烯基三苯基鏻盐，其与共轭碱发生迈克尔加成反应以产生稳定的磷叶立德。发现硅胶粉末在无溶剂条件下，在微波辐射（0.72 KW，9 分钟）或热条件（95°C，45 分钟）下催化稳定的磷叶立德转化为相应的缺电子 2H-色烯。相当不错的收益。

  DOI：

  10.1080/10426500600864395

文献信息

• 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。
• Copper oxide catalyzed domino process for the synthesis of substituted 2H-pyran-2-ones and polyhydroxy coumarin derivatives
  作者：Utpal Kayal、Rajiv Karmakar、Dipanwita Banerjee、Gourhari Maiti

  DOI：10.1016/j.tet.2014.07.032

  日期：2014.9
• 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.
• Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates
  作者：Farough Nasiri、Kourosh Pourdavaie、Samiyeh Yosefdad、Bahareh Atashkar

  DOI：10.1016/j.mencom.2007.11.019

  日期：2007.11

  The reaction of dialkyl acetylenedicarboxylates with six-membered cyclic 1,3-diketones such as 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione in the presence of a catalytic amount of trimethylamine, triethylamine or tributylamine in CH(2)Cl(2) leads to alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates in good yields.