methyl 4-oxo-1,4-dihydrochromeno[2,3-b]pyrrole-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 4-oxo-1,4-dihydrochromeno[2,3-b]pyrrole-2-carboxylate
• 英文别名: methyl 4-oxo-1H-chromeno[2,3-b]pyrrole-2-carboxylate
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: KAVLKLPGIOXGKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基苯乙酮 在 potassium carbonate 、 silver(l) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.0h， 生成 methyl 4-oxo-1,4-dihydrochromeno[2,3-b]pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of Functionalized Chromeno[2,3-b]pyrrol-4(1H)-ones by Silver-Catalyzed Cascade Reactions of Chromones/Thiochromones and Isocyanoacetates

  摘要：

  A novel and convenient approach to the synthesis of chromeno[2,3-b]pyrrol-4(1H)-ones has been developed. Furthermore, the method involves a facile silver-catalyzed cascade cyclization reaction including an intramolecular C-O bond formation. The silver salt acts as a key promoter.

  DOI：

  10.1021/acs.orglett.5b02795

文献信息

• 2-(N-Methylanilino)-3-formylchromone—a versatile synthon for incorporation of chromone moiety in a variety of heterocyclic systems and macrocycles through reactions with bifunctional nucleophiles
  作者：Gurmit Singh、Lakhwinder Singh、M.P.S Ishar

  DOI：10.1016/s0040-4020(02)00908-0

  日期：2002.9

  2-(N-methylanilino)-3-formylchromones with a number of bifunctional nucleophiles, involving substitution of N-methylanilino moiety and/or condensations with 3-formyl function have provided an easy access to a variety of potentially biologically active hetero-annelated chromones, novel macrocycles, and tetradentate ligands having intact chromone moiety.

  2-（N-甲基苯胺基）-3-甲酰基色酮与许多双功能亲核试剂的反应，包括N-甲基苯胺基部分的取代和/或3-甲酰基官能团的缩合，提供了容易获得的多种潜在的具有生物活性的杂原子-色酮，新型大环和具有完整色酮部分的四齿配体。
• Synthesis of Chromeno[2,3-<i>d</i>]imidazol-9(1<i>H</i>)-ones via Tandem Reactions of 3-Iodochromones with Amidines Involving Copper-Catalyzed C–H Functionalization and C–O Bond Formation
  作者：Jia Sheng、Bo Chao、Hong Chen、Youhong Hu

  DOI：10.1021/ol401966y

  日期：2013.9.6

  A novel six-membered heterocyclic skeleton of imidazochromone was prepared via an efficient one-pot reaction including a key step of copper-catalyzed aerobic C-H intramolecular cycloetherification. Notably, this process does not require the presence of strong para electron-withdrawing groups on the phenol component. Also, the results of this effort show that acyl phenols containing electron-rich heterocycles participate in an efficient C-H activation/C-O formation process.
• Synthesis of Functionalized Chromeno[2,3-<i>b</i>]pyrrol-4(1<i>H</i>)-ones by Silver-Catalyzed Cascade Reactions of Chromones/Thiochromones and Isocyanoacetates
  作者：Xueyu Qi、Haoyue Xiang、Chunhao Yang

  DOI：10.1021/acs.orglett.5b02795

  日期：2015.11.20

  A novel and convenient approach to the synthesis of chromeno[2,3-b]pyrrol-4(1H)-ones has been developed. Furthermore, the method involves a facile silver-catalyzed cascade cyclization reaction including an intramolecular C-O bond formation. The silver salt acts as a key promoter.