ethyl 5,6-dihydroxy-2,7-dimethylbenzofuran-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 5,6-dihydroxy-2,7-dimethylbenzofuran-3-carboxylate
• 英文别名: ethyl 5,6-dihydroxy-2,7-dimethyl-1-benzofuran-3-carboxylate；ethyl 5,6-dihydroxy-2,7-dimethylbenzo[b]furan-3-carboxylate
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: SYGXWAUTFNMPJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯乙酰乙酸乙酯 、 3-甲基苯邻二酚 以 水 、 乙腈 为溶剂， 以80%的产率得到ethyl 5,6-dihydroxy-2,7-dimethylbenzofuran-3-carboxylate
  参考文献：
  名称：

  在-2-氯乙酰乙酸乙酯存在下，儿茶酚的电化学氧化。综合与机理研究

  摘要：

  使用循环伏安法和可控电库仑法在水/乙腈（90:10）溶液中存在2-氯乙酰乙酸乙酯（3）的情况下，研究了邻苯二酚和一些3-取代的邻苯二酚（1a-c）的电化学氧化。结果表明，衍生自邻苯二酚（1a-c）的醌与-2-氯乙酰乙酸乙酯（3）参与迈克尔加成反应，每1分子仅消耗两个电子，形成相应的苯并呋喃（10a-c）。 。苯并呋喃的电化学合成（10a-c）已成功地在碳棒电极和未分割的电解槽中进行，具有良好的产率和纯度。提出了一种新的电极双电子机理。

  DOI：

  10.1002/jhet.5570430638

文献信息

• Cocatalytic Enzyme System for the Michael Addition Reaction of in-situ-Generated<i>ortho</i>-Quinones
  作者：Suteera Witayakran、Arthur J. Ragauskas

  DOI：10.1002/ejoc.200800791

  日期：2009.1

  A laccase-lipase cocatalytic system was used to catalyze the domino reaction between catechols and nucleophilic reagents including 1,3-dicarbonyl compounds and aromatic amines in aqueous medium at room temperature. Lipase acted as a catalyst for Michael addition step, and also enhanced the overall yield of the final products. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  漆酶-脂肪酶共催化系统用于在室温下在水性介质中催化儿茶酚与亲核试剂（包括 1,3-二羰基化合物和芳香胺）之间的多米诺骨牌反应。脂肪酶作为迈克尔加成步骤的催化剂，也提高了最终产品的总产率。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Cascade synthesis of benzofuran derivatives via laccase oxidation–Michael addition
  作者：Suteera Witayakran、Leslie Gelbaum、Arthur J. Ragauskas

  DOI：10.1016/j.tet.2007.08.066

  日期：2007.11

  The cascade synthesis of benzofuran derivatives was conducted from the reaction of catechols and 1,3-dicarbonyl compounds via oxidation - Michael addition in the presence of laccase and Sc(OTf)(3)/SDS. This reaction was carried out under air at room temperature in aqueous medium, and provided benzofuran products in moderate to good yields. In addition, this reaction system showed recyclability. Published by Elsevier Ltd.
• Electrochemical synthesis of 5,6-dihydroxy-2-methyl-1-benzofuran-3-carboxylate derivatives
  作者：Ali Reza Fakhari、Davood Nematollahi、Mojtaba Shamsipur、Somayeh Makarem、Seyed Saeid Hosseini Davarani、Abdolali Alizadeh、Hamid Reza Khavasi

  DOI：10.1016/j.tet.2007.02.023

  日期：2007.4

  Electrochemical oxidation of catechols (1a-c) has been studied in the presence of methyl acetoacetate (2a) and ethyl acetoacetate (2b) as nucleophiles in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols (1a-c) participate in Michael addition reactions with 2a and 2b to form the corresponding benzofuran derivatives (3a-f). The electrochemical synthesis of 3a-f has been successfully performed in an undivided cell in good yield and purity. The oxidation mechanism was deduced from voltammetric data and by coulometry at controlled potential. The products have been characterized after purification by IR, H-1 NMR, C-13 NMR, MS, and single crystal X-ray diffraction. (C) 2007 Elsevier Ltd. All rights reserved.