5-methoxybenzofuran-3-yl acetate | 60770-33-4

• 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: 5-methoxybenzofuran-3-yl acetate
• 英文别名: 3-acetoxy-5-methoxy-benzofuran；5-Methoxy-3-acetoxybenzofuran；(5-Methoxy-1-benzofuran-3-yl) acetate
• CAS: 60770-33-4
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: UCQSDMBSIQVHTP-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C
• 沸点：
  175 °C(Press: 13 Torr)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxybenzofuran-3-yl acetate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 5-甲氧基-3-苯并呋喃酮
  参考文献：
  名称：

  具有双5-HT 1A受体和5-羟色胺转运蛋白亲和力的新型苯并呋喃衍生物

  摘要：

  制备了几种通过烷基链与3-吲哚四氢吡啶连接的苯并呋喃衍生物，并评估了其血清素转运蛋白和5-HT 1A受体的亲和力。描述了它们的设计，合成和结构-活性关系。

  DOI：

  10.1016/j.bmcl.2009.12.093
• 作为产物：
  描述：

  methyl 2-((ethoxycarbonyl)methoxy)-5-methoxybenzoate 在 sodium acetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 5-methoxybenzofuran-3-yl acetate
  参考文献：
  名称：

  利用脱羧不对称烯丙基烷基化在苯并呋喃-3(2H)-Ones中不对称合成季α-芳基立构中心

  摘要：

  Pd 催化的脱羧不对称烯丙基烷基化 (DAAA) 已开发用于空间位阻苯并呋喃-3(2 H )-酮衍生的 α-芳基-β-酮酯。底物合成的关键步骤采用了先前开发的 Pb 介导的 α-芳基化。 17 个 DAAA 实例的底物范围表明，芳环上含有二邻位取代模式的底物以及含有萘基的底物产生了高达 96% ee的最高对映选择性。

  DOI：

  10.1002/chem.202401738

文献信息

• Novel benzofuran derivatives with dual 5-HT1A receptor and serotonin transporter affinity
  作者：Aranapakam M. Venkatesan、O. Dos Santos、John Ellingboe、Deborah A. Evrard、Boyd L. Harrison、Deborah L. Smith、Rosemary Scerni、Geoffrey A. Hornby、Lee E. Schechter、Terrence H. Andree

  DOI：10.1016/j.bmcl.2009.12.093

  日期：2010.2

  Several benzofuran derivatives linked to a 3-indoletetrahydropyridine through an alkyl chain were prepared and evaluated for serotonin transporter and 5-HT1A receptor affinities. Their design, synthesis and structure–activity relationships are described.

  制备了几种通过烷基链与3-吲哚四氢吡啶连接的苯并呋喃衍生物，并评估了其血清素转运蛋白和5-HT 1A受体的亲和力。描述了它们的设计，合成和结构-活性关系。
• Synthesis, antibacterial activity, and quantitative structure–activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3()-benzofuranone derivatives
  作者：Narges Hadj-esfandiari、Latifeh Navidpour、Hooman Shadnia、Mohsen Amini、Nasrin Samadi、Mohammad Ali Faramarzi、Abbas Shafiee

  DOI：10.1016/j.bmcl.2007.09.062

  日期：2007.11

  A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities. (C) 2007 Elsevier Ltd. All rights reserved.
• CAGNIANT P.; KIRSCH G., C. R. ACAD. SCI <CHDC-AQ>, 1976, C 282, NO 21, 993-996
  作者：CAGNIANT P.、 KIRSCH G.

  DOI：——

  日期：——
• TURAN-ZITOUNI G.; FULCRAND P., CHIM. ACTA TURC., 13,(1985) N 3, 403-412
  作者：TURAN-ZITOUNI G.、 FULCRAND P.

  DOI：——

  日期：——
• 99mTc/Re complexes based on flavone and aurone as SPECT probes for imaging cerebral β-amyloid plaques
  作者：Masahiro Ono、Ryoichi Ikeoka、Hiroyuki Watanabe、Hiroyuki Kimura、Takeshi Fuchigami、Mamoru Haratake、Hideo Saji、Morio Nakayama

  DOI：10.1016/j.bmcl.2010.08.004

  日期：2010.10

  Two Tc-99m/Re complexes based on flavone and aurone were tested as potential probes for imaging beta-amyloid plaques using single photon emission computed tomography. Both Tc-99m-labeled derivatives showed higher affinity for A beta(1-42) aggregates than did Tc-99m-BAT. In sections of brain tissue from an animal model of AD, the Re-flavone derivative 9 and Re-aurone derivative 19 intensely stained beta-amyloid plaques. In biodistribution experiments using normal mice, Tc-99m-labeled flavone and aurone displayed similar radioactivity pharmacokinetics. With additional modifications to improve their brain uptake, Tc-99m complexes based on the flavone or aurone scaffold may serve as probes for imaging cerebral beta-amyloid plaques. (C) 2010 Elsevier Ltd. All rights reserved.