4-n-propyl-2,3,4,5-tetrahydro-7-methyl-2,5-dioxo-pyrano[4,3-b]pyran-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-n-propyl-2,3,4,5-tetrahydro-7-methyl-2,5-dioxo-pyrano[4,3-b]pyran-3-carboxylic acid
• 英文别名: (3S,4R)-7-methyl-2,5-dioxo-4-propyl-3,4-dihydropyrano[3,2-c]pyran-3-carboxylic acid
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: JFVSSYYADMGEKZ-XVKPBYJWSA-N

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：
  0.46
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 丙二酸环(亚)异丙酯 、 正丁醛 在 tetramethylguanidinium trifluoromethanesulfonate 作用下， 反应 0.75h， 以84%的产率得到4-n-propyl-2,3,4,5-tetrahydro-7-methyl-2,5-dioxo-pyrano[4,3-b]pyran-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of 4-substituted pyrano[4,3-b]pyran-2,5-diones in an ionic liquid

  摘要：

  The mildly basic ionic liquid N,N,N,N-tetramethylguanidinium triflate (TMGTf) was found to be a very effective solvent for the reaction between 4-hydroxy-6-methyl-2H-pyran-2-one, Meldrum's acid, and aldehydes to afford some novel pyrano[4,3-b]pyran-2,5-diones in high yields at room temperature. The stages, through which these reactions might proceed, depend largely on the nature of the aldehyde substrates. The reaction of aliphatic aldehydes has given access to some novel carboxylated products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.113

文献信息

• Synthesis of 4-substituted pyrano[4,3-b]pyran-2,5-diones in an ionic liquid
  作者：Kurosh Rad-Moghadam、Masoumeh Sharifi-Kiasaraie、Seyyedeh Cobra Azimi

  DOI：10.1016/j.tet.2012.05.113

  日期：2012.8

  The mildly basic ionic liquid N,N,N,N-tetramethylguanidinium triflate (TMGTf) was found to be a very effective solvent for the reaction between 4-hydroxy-6-methyl-2H-pyran-2-one, Meldrum's acid, and aldehydes to afford some novel pyrano[4,3-b]pyran-2,5-diones in high yields at room temperature. The stages, through which these reactions might proceed, depend largely on the nature of the aldehyde substrates. The reaction of aliphatic aldehydes has given access to some novel carboxylated products. (C) 2012 Elsevier Ltd. All rights reserved.