4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one | 106751-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one
• 英文别名: 4-methoxy-furo[3,2-g]chromen-5-one；4-Methoxy-furo[3,2-g]chromen-5-on；Visnagin；4-Methoxyfuro[3,2-g]chromen-5-one
• CAS: 106751-60-4
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: QSHAGOXSQXSYJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以76%的产率得到4-methoxy-6,7-dihydro-5H-furo[3,2-g][1]benzopyran-5-one
  参考文献：
  名称：

  Linearly Fused Furochromones by Intramolecular Enaminone Reactions

  摘要：

  合成了一系列新的线性融合呋喃色酮。该方法是从天然存在的维斯纳金和赫林出发，通过使用N，N-二甲基甲酰胺二甲醚进行恩酰酮形成，然后在酸性介质中进行环闭合。描述了对恩酰酮衍生物的各种反应。

  DOI：

  10.1515/znb-2002-0513
• 作为产物：
  描述：

  1-(4-methoxy-6-hydroxy-benzofuran-5-yl)-3-dimethyl-amino-2-propen-1-one 在 溶剂黄146 作用下， 反应 5.0h， 以92%的产率得到4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one
  参考文献：
  名称：

  Linearly Fused Furochromones by Intramolecular Enaminone Reactions

  摘要：

  合成了一系列新的线性融合呋喃色酮。该方法是从天然存在的维斯纳金和赫林出发，通过使用N，N-二甲基甲酰胺二甲醚进行恩酰酮形成，然后在酸性介质中进行环闭合。描述了对恩酰酮衍生物的各种反应。

  DOI：

  10.1515/znb-2002-0513

文献信息

• 4-Phenoxybutoxy-substituted heterocycles – A structure–activity relationship study of blockers of the lymphocyte potassium channel Kv1.3
  作者：Silke B. Bodendiek、Cédrick Mahieux、Wolfram Hänsel、Heike Wulff

  DOI：10.1016/j.ejmech.2008.10.033

  日期：2009.5

  The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC(50) of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC(50)s of 150 nM to 10 mu M in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC(50) 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin
  作者：Alexander Schönberg、Nasry Badran、Nicolas A. Starkowsky

  DOI：10.1021/ja01116a032

  日期：1953.10
• On Visnagin and Khellin and Related Compounds. A Simple Synthesis of Chromone
  作者：Alexander Schönberg、Aly Sina

  DOI：10.1021/ja01164a022

  日期：1950.8
• EL-SHARIEF, A. M. SH.;EL-MAGHRABY, A. A.;ZAHER, M. R.;MOHAMED, Y. A., EGYPT. J. CHEM., 1984, 27, N 4, 443-458
  作者：EL-SHARIEF, A. M. SH.、EL-MAGHRABY, A. A.、ZAHER, M. R.、MOHAMED, Y. A.

  DOI：——

  日期：——
• Linearly Fused Furochromones by Intramolecular Enaminone Reactions
  作者：Abdel-Rahman H. Abdel-Rahmana、Eman M. Keshk、Emad M. El-Telbani

  DOI：10.1515/znb-2002-0513

  日期：2002.5.1

  A number of new linearly fused furochromones were synthesized. The methodology was performed starting from naturally occurring visnagin and khellin via enaminone formation using N,N-dimethyl formamide dimethylacetal followed by ring closure in acidic medium. Various reactions on the enaminone derivatives are described.

  合成了一系列新的线性融合呋喃色酮。该方法是从天然存在的维斯纳金和赫林出发，通过使用N，N-二甲基甲酰胺二甲醚进行恩酰酮形成，然后在酸性介质中进行环闭合。描述了对恩酰酮衍生物的各种反应。