4-(4-methoxyphenyl)-7-methyl-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-2,5-dione | 1384931-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-7-methyl-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-2,5-dione
• 英文别名: 4-(4-methoxyphenyl)-7-methyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione；4-(4-Methoxyphenyl)-7-methyl-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-2,5-dione；4-(4-methoxyphenyl)-7-methyl-3,4-dihydropyrano[3,2-c]pyran-2,5-dione
• CAS: 1384931-39-8
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: PDOGOXFDIDEVGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 (Z)-2-bromo-3-(4-methoxyphenyl)acrylaldehyde 在 caesium carbonate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 以77%的产率得到4-(4-methoxyphenyl)-7-methyl-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-2,5-dione
  参考文献：
  名称：

  NHC催化环戊酸修饰的环烯环化反应合成功能化香豆素和喹啉酮

  摘要：

  据报道，N-杂环卡宾（NHC）催化2-溴烯醛的内酯化和杂环CHH酸的内酰胺化，通过α，β-不饱和酰基偶氮中间体进行。该反应提供了香豆素或喹啉酮融合的内酯/内酰胺衍生物。另外，提供了使用手性NHC的该反应的对映选择性形式的结果。

  DOI：

  10.1021/jo500693h

文献信息

• Synthesis of 4-Aryl-7-Methyl-3,4-Dihydropyrano[4,3-b]Pyran-2,5-Dione by Three-Component and One-Pot Reaction
  作者：Esmat Hashemzaei、Alireza Hassanabadi

  DOI：10.3184/174751915x14360063655029

  日期：2015.7

  Three-component and one-pot, reaction between 4-hydroxy-6-methyl-2H-pyran-2-one, Meldrum's acid and aryl aldehydes in the presence of piperidine affords 4-aryl-7-methyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione in excellent yields.

  三组分一锅，4-羟基-6-甲基-2H-吡喃-2-酮、Meldrum酸和芳基醛在哌啶存在下反应得到4-芳基-7-甲基-3,4-二氢吡喃[4,3-b]pyran-2,5-dione 产率极好。
• 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.
• Synthesis of Functionalized Coumarins and Quinolinones by NHC-Catalyzed Annulation of Modified Enals with Heterocyclic C–H Acids
  作者：Santhivardhana Reddy Yetra、Tony Roy、Anup Bhunia、Digvijay Porwal、Akkattu T. Biju

  DOI：10.1021/jo500693h

  日期：2014.5.2

  N-Heterocyclic carbene (NHC) catalyzed lactonization and lactamization of 2-bromoenals with heterocyclic C–H acids proceeding via the α,β-unsaturated acyl azolium intermediates is reported. The reaction furnished coumarin- or quinolinone-fused lactone/lactam derivatives. In addition, results of the enantioselective version of this reaction using chiral NHC are presented.

  据报道，N-杂环卡宾（NHC）催化2-溴烯醛的内酯化和杂环CHH酸的内酰胺化，通过α，β-不饱和酰基偶氮中间体进行。该反应提供了香豆素或喹啉酮融合的内酯/内酰胺衍生物。另外，提供了使用手性NHC的该反应的对映选择性形式的结果。