1-(8-羟基二苯并呋喃-2-基)乙酮 | 744253-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 1-(8-羟基二苯并呋喃-2-基)乙酮
• 英文名称: 8-hydroxydibenzofuran-2-yl methyl ketone
• 英文别名: 1-(8-Hydroxydibenzofuran-2-yl)ethanone
• CAS: 744253-95-0
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: PYFVVRGWNYMJHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(8-羟基二苯并呋喃-2-基)乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper dichloride 作用下， 以 邻二氯苯 、 乙腈 为溶剂， 反应 17.0h， 生成 10-acetyl-3,3-dimethyl-3H-benzofuro[3,2-f][1]benzopyran
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of benzofurobenzopyran analogues

  摘要：

  We recently reported that 3,3-dimethyl-3H-benzofuro[3,2,f][1]-benzopyran and its hydrogenated analogue are selective in vitro inhibitors of mycobacterial growth. However, their lack of in vivo activity on a murine model of Mycobacterium tuberculosis infection due to their poor bioavailability led to a structure-activity relationship investigation. We wish to report here the preparation of some structural analogues along with their biological effect on the growth of Mycobacterium smegmatis, M. tuberculosis, as well as on VERO cells for the most active compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.009
• 作为产物：
  描述：

  2-羟基二苯并呋喃 在 吡啶 、 三氯化铝 作用下， 反应 3.25h， 生成 1-(8-羟基二苯并呋喃-2-基)乙酮
  参考文献：
  名称：

  Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions

  摘要：

  The Fries rearrangement of dibenzofuran-2-yl ethanoate as a route to o-hydroxyacetyidibenzofurans has been investigated, both under thermal Lewis-acid catalysed and non-catalysed photochemical conditions. The reactions were examined theoretically at semi-empirical (PM3 and ZINDO/S) and density functional theory (DFT) levels. The correct selection of reaction conditions provides viable preparative routes to ortho-acylated hydroxydibenzofurans. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.060

文献信息

• [EN] PYRANODIBENZOFURAN DERIVATIVES WITH ANTIFUNGAL AND ANTIBACTERIAL ACTIVITY<br/>[FR] DÉRIVÉS DE PYRANODIBENZOFURANE PRÉSENTANT UNE ACTIVITÉ ANTIFONGIQUE ET ANTIBACTÉRIENNE
  申请人：PASTEUR INSTITUT

  公开号：WO2007039609A1

  公开（公告）日：2007-04-12

  [EN] Compound of the general formula (I): and in particular compounds of formula (II), (III), (IV), their process of preparation and their use as medicament for the treatment of fungal or bacterial infections, in particular mycobacterial infection.
  [FR] La présente invention a pour objet un composé de formule générale (I) : et en particulier les composés de formule (II), (III), (IV), leur procédé de synthèse et leur emploi en tant que médicament dans le traitement d'infections fongiques ou bactériennes, en particulier d'une infection mycobactérienne.
• Synthesis and antimycobacterial evaluation of benzofurobenzopyran analogues
  作者：Soizic Prado、Yves L. Janin、Brigitte Saint-Joanis、Priscille Brodin、Sylvie Michel、Michel Koch、Stewart T. Cole、François Tillequin、Pierre-Etienne Bost

  DOI：10.1016/j.bmc.2006.12.009

  日期：2007.3

  We recently reported that 3,3-dimethyl-3H-benzofuro[3,2,f][1]-benzopyran and its hydrogenated analogue are selective in vitro inhibitors of mycobacterial growth. However, their lack of in vivo activity on a murine model of Mycobacterium tuberculosis infection due to their poor bioavailability led to a structure-activity relationship investigation. We wish to report here the preparation of some structural analogues along with their biological effect on the growth of Mycobacterium smegmatis, M. tuberculosis, as well as on VERO cells for the most active compound. (c) 2006 Elsevier Ltd. All rights reserved.
• Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions
  作者：Ana M.A.G Oliveira、Ana M.F Oliveira-Campos、M.Manuela M Raposo、John Griffiths、Antonio E.H Machado

  DOI：10.1016/j.tet.2004.05.060

  日期：2004.7

  The Fries rearrangement of dibenzofuran-2-yl ethanoate as a route to o-hydroxyacetyidibenzofurans has been investigated, both under thermal Lewis-acid catalysed and non-catalysed photochemical conditions. The reactions were examined theoretically at semi-empirical (PM3 and ZINDO/S) and density functional theory (DFT) levels. The correct selection of reaction conditions provides viable preparative routes to ortho-acylated hydroxydibenzofurans. (C) 2004 Elsevier Ltd. All rights reserved.