3-(methoxycarbonyl)furan-2-carboxylic acid | 23268-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(methoxycarbonyl)furan-2-carboxylic acid
• 英文别名: 3-methoxycarbonylfuran-2-carboxylic acid
• CAS: 23268-41-9
• 化学式: C₇H₆O₅
• mdl: MFCD28246543
• 分子量: 170.122
• InChiKey: WULAGCQNPNLHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠酸（呋喃甲酸） 、 氰基甲酸甲酯 在 正丁基锂 作用下， 以 氘代四氢呋喃 、 正己烷 、 四氢呋喃 为溶剂， 反应 4.33h， 生成 5-甲氧基羰基呋喃-2-羧酸 、 3-(methoxycarbonyl)furan-2-carboxylic acid
  参考文献：
  名称：

  The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products

  摘要：

  Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is alos useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.

  DOI：

  10.1021/np300468h

文献信息

• Production of 2,5‐Furandicarboxylic Acid Methyl Esters from Pectin‐Based Aldaric Acid: from Laboratory to Bench Scale
  作者：Nicolaas van Strien、Jukka Niskanen、Anneloes Berghuis、Holger Pöhler、Sari Rautiainen

  DOI：10.1002/cssc.202300732

  日期：2024.1.8

  The synthesis and purification of pectin-based 2,5-furandicarboxylic acid methyl esters from gram-scale to kilogram-scale enables the valorisation of agricultural side streams into fully renewable polyesters.

  果胶基 2,5-呋喃二甲酸甲酯的合成和纯化（从克级到公斤级）能够将农业副产品增值为完全可再生的聚酯。
• The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products
  作者：Christian A. Citron、Patrick Rabe、Jeroen S. Dickschat

  DOI：10.1021/np300468h

  日期：2012.10.26

  Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is alos useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.