9-Bromo-3,7-dimethoxy-[1]benzofuro[3,2-b]chromen-11-one | 406214-63-9

• 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: 9-Bromo-3,7-dimethoxy-[1]benzofuro[3,2-b]chromen-11-one
• CAS: 406214-63-9
• 化学式: C₁₇H₁₁BrO₅
• 分子量: 375.175
• InChiKey: SMDPLZRJABPNIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Bromo-3,7-dimethoxy-[1]benzofuro[3,2-b]chromen-11-one 在 吡啶盐酸盐 作用下， 生成 1-Bromo-3,7-dihydroxy-5,11-dioxa-benzo[b]fluoren-10-one
  参考文献：
  名称：

  Constrained phytoestrogens and analogues as ERβ selective ligands

  摘要：

  A new series of ERbeta (ERbeta) selective ligands has been prepared. One of the compounds 6, structurally related to the phytoestrogen apigenin 4, displays a binding preference for ERbeta over ERalpha of over 40-fold. In addition to its binding selectivity, 6 was able to potently induce metallothionein (an ERbeta specific response in human SAOS-2 cells) while demonstrating low potency in an ERalpha dependant ERE-tk luciferase assay in MCF-7 cells. Such receptor and cell selectivity could make 6 a useful molecular probe for better understanding the role of ERbeta in mammalian physiology. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00394-9
• 作为产物：
  描述：

  3-溴-2-羟基-5-甲氧基苯甲酸甲酯 、 2-chloro-1-(2-fluoro-4,6-dimethoxy-phenyl)-ethanone 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到9-Bromo-3,7-dimethoxy-[1]benzofuro[3,2-b]chromen-11-one
  参考文献：
  名称：

  A highly efficient, one-pot synthesis of benzo[b]fluoren-10-ones

  摘要：

  5,[1-Dioxa- and 5-oxa-1]-thiabenzo[b]fluoren-10-ones were prepared via a one-pot procedure initiated by the reaction of salicylates or thiasalicylates with ortho fluoro-alpha -bromoacetophenones in the presence of cesium carbonate. The reactions proceeded in good yield and the final products were obtained without chromatography. The reaction presumably proceeds via a sequential intermolecular alkylation, intramolecular acylation sequence concluded by an intramolecular, ipso-fluoro substitution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01828-7

文献信息

• A highly efficient, one-pot synthesis of benzo[b]fluoren-10-ones
  作者：Michael D. Collini、Chris P. Miller

  DOI：10.1016/s0040-4039(01)01828-7

  日期：2001.11

  5,[1-Dioxa- and 5-oxa-1]-thiabenzo[b]fluoren-10-ones were prepared via a one-pot procedure initiated by the reaction of salicylates or thiasalicylates with ortho fluoro-alpha -bromoacetophenones in the presence of cesium carbonate. The reactions proceeded in good yield and the final products were obtained without chromatography. The reaction presumably proceeds via a sequential intermolecular alkylation, intramolecular acylation sequence concluded by an intramolecular, ipso-fluoro substitution. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Constrained phytoestrogens and analogues as ERβ selective ligands
  作者：Chris P Miller、Michael D Collini、Heather A Harris

  DOI：10.1016/s0960-894x(03)00394-9

  日期：2003.7

  A new series of ERbeta (ERbeta) selective ligands has been prepared. One of the compounds 6, structurally related to the phytoestrogen apigenin 4, displays a binding preference for ERbeta over ERalpha of over 40-fold. In addition to its binding selectivity, 6 was able to potently induce metallothionein (an ERbeta specific response in human SAOS-2 cells) while demonstrating low potency in an ERalpha dependant ERE-tk luciferase assay in MCF-7 cells. Such receptor and cell selectivity could make 6 a useful molecular probe for better understanding the role of ERbeta in mammalian physiology. (C) 2003 Elsevier Science Ltd. All rights reserved.