1-(4'-acetyl-5,5'-dihydroxy-2',3'-dihydro[2,3']bibenzofuran-4-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-(4'-acetyl-5,5'-dihydroxy-2',3'-dihydro[2,3']bibenzofuran-4-yl)ethanone
• 英文别名: 1-[2-(4-Acetyl-5-hydroxy-2,3-dihydro-1-benzofuran-3-yl)-5-hydroxy-1-benzofuran-4-yl]ethanone；1-[2-(4-acetyl-5-hydroxy-2,3-dihydro-1-benzofuran-3-yl)-5-hydroxy-1-benzofuran-4-yl]ethanone
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: ZHXNAYWCPOIMMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 Amberlyst 15 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-(4'-acetyl-5,5'-dihydroxy-2',3'-dihydro[2,3']bibenzofuran-4-yl)ethanone
  参考文献：
  名称：

  A Controlled Synthesis of Nature-Mimicking Benzofurans and their Corresponding Dimers

  摘要：

  羟基和乙酰基官能化的苯并呋喃不仅是大量生物活性天然产物中的核心结构，也是多种天然存在的呋喃黄酮类化合物的重要前体。文献中提供了许多合成官能化苯并呋喃的方法，但关于邻位羟基和乙酰基官能化苯并呋喃的文献却很少。本文中，我们报道了从易得的前体出发，高度便捷地合成仿生苯并呋喃及其二聚体的方法。

  DOI：

  10.1055/s-2006-944194

文献信息

• Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors
  作者：Manish Dixit、Brajendra K. Tripathi、Akhilesh K. Tamrakar、Arvind K. Srivastava、Brijesh Kumar、Atul Goel

  DOI：10.1016/j.bmc.2006.10.053

  日期：2007.1

  Protein tyrosine phosphatase 113 (PTP-1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP-1B knockout mice showed increased insulin sensitivity in muscle and liver as well as resistance to obesity. A series of hydroxy benzofuran methyl ketones and their naturally mimicking dimers and linear and angular furanochalcones and flavones have been evaluated as PTP-1B inhibitors. Screened compounds displayed good inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.
• A Controlled Synthesis of Nature-Mimicking Benzofurans and their Corresponding Dimers
  作者：Atul Goel、Manish Dixit、Ashoke Sharon、Prakas Maulik

  DOI：10.1055/s-2006-944194

  日期：2006.6

  Benzofurans functionalized with hydroxy and acetyl functionalities are not only the core structures found in a large number of biologically important natural products, but also the vital precursors for several naturally occurring furanoflavonoids. Numerous synthetic methodologies are available in the literature for the ­synthesis of functionalized benzofurans but access to benzofurans with adjacent hydroxy and acetyl functionalities shows paucity of references. In this paper we report highly convenient synthesis of nature-mimicking benzofurans and their dimers from easily accessible precursors.

  羟基和乙酰基官能化的苯并呋喃不仅是大量生物活性天然产物中的核心结构，也是多种天然存在的呋喃黄酮类化合物的重要前体。文献中提供了许多合成官能化苯并呋喃的方法，但关于邻位羟基和乙酰基官能化苯并呋喃的文献却很少。本文中，我们报道了从易得的前体出发，高度便捷地合成仿生苯并呋喃及其二聚体的方法。