1-(5,6-dihydroxy-2-methyl-1-benzofuran-3-yl)ethanone

• 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: 1-(5,6-dihydroxy-2-methyl-1-benzofuran-3-yl)ethanone
• 英文别名: 3-acetyl-5,6-dihydroxy-2-methylbenzofuran；Ethanone, 1-(5,6-dihydroxy-2-methyl-3-benzofuranyl)-(9CI)
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: HSWRQRBMNFLILB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯邻苯二酚 、 乙酰丙酮 在 lipase from Pseudomonas Cepacia 、 laccase from Trametes Villosa 作用下， 反应 4.0h， 以8%的产率得到1-(5,6-dihydroxy-2-methyl-1-benzofuran-3-yl)ethanone
  参考文献：
  名称：

  原位生成邻醌迈克尔加成反应的助催化酶系统

  摘要：

  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)

  DOI：

  10.1002/ejoc.200800791

文献信息

• One-Pot Laccase-Catalysed Synthesis of 5,6-Dihydroxylated Benzo[<i>b</i>]furans and Catechol Derivatives, and Their Anticancer Activity
  作者：Kevin W. Wellington、Tozama Qwebani-Ogunleye、Natasha I. Kolesnikova、Dean Brady、Charles B. de Koning

  DOI：10.1002/ardp.201200413

  日期：2013.4

  A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6‐dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer

  来自 Novozymes 的商用漆酶 Suberase® 用于催化 5,6-二羟基苯并 [b] 呋喃和儿茶酚衍生物的合成。在某些情况下，产量类似于或优于通过其他酶促、化学或电化学合成获得的产量。合成的衍生物针对肾 (TK10)、黑色素瘤 (UACC62)、乳腺癌 (MCF7) 和宫颈 (HeLa) 癌细胞系进行筛选。GI50、TGI和LC50是首次报道。抗癌筛查表明，5,6-二羟基苯并[b]呋喃的细胞抑制作用对黑色素瘤（UACC62）癌细胞系最有效，其中几种化合物表现出有效的生长抑制活性（GI50 = 0.77–9.76 µM），其中两种化合物的活性优于抗癌剂依托泊苷 (GI50 = 0.89 µM)。一种化合物对肾 (TK10) 癌细胞系表现出强效活性 (GI50 = 9.73 µM)，两种化合物对乳腺癌 (MCF7) 癌细胞系表现出强效活性 (GI50 = 8.79 和 9.30 µM)。这些结果鼓励对
• One-pot synthesis of 5,6-dihydroxylated benzo[b]furan derivatives
  作者：Li-Xia Pei、Yue-Ming Li、Xian-Zhang Bu、Lian-Quan Gu、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2006.02.055

  日期：2006.4

  presence of sodium iodate and pyridine, several 5,6-dihydroxylated benzo[b]furan derivatives were synthesized via oxidation–Michael addition of β-dicarbonyl compounds with catechols in a one-pot procedure. The final products were confirmed by ESMS, NMR, and single-crystal X-ray diffraction study. The mechanism different from that of electrochemical methods was proposed based on DFT calculation.

  在碘酸钠和吡啶存在下，通过一锅法将β-二羰基化合物与邻苯二酚进行氧化-迈克尔加成反应，合成了5,6-二羟基化的苯并[ b ]呋喃衍生物。最终产物通过ESMS，NMR和单晶X射线衍射研究确认。基于DFT计算，提出了不同于电化学方法的机理。
• 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.