methyl 4-(2-bromo-4-methoxyphenoxy)but-2-enoate | 589090-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-(2-bromo-4-methoxyphenoxy)but-2-enoate
• 英文别名: methyl (E)-4-(2-bromo-4-methoxyphenoxy)but-2-enoate
• CAS: 589090-73-3
• 化学式: C₁₂H₁₃BrO₄
• 分子量: 301.137
• InChiKey: ZCLDQZVBWWFMKY-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-bromo-4-methoxyphenoxy)but-2-enoate 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (+/-)-2-(5-methoxy-2,3-dihydrobenzofuran-3-yl)ethyl p-toluenesulfonate
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of a Series of Geometrically Constrained 5-HT_2A/2C Receptor Ligands

  摘要：

  In studies of the SAR of phenethylamine-type serotonin 5-HT2A receptor agonists, substituted conformationally constrained tetrahydronaphthofurans were designed to investigate the optimal conformation of the 2-aminoethyl moiety. These compounds were tested using in vitro assays for affinity at 5-HT1A, 5-HT2A, and 5-HT2C receptors. The benzofuran-containing analogues, 6a and 6b, had significantly higher affinity for the 5-HT receptors tested than did the benzodi-hydrofuran-containing compounds, 4a, 4b, 5a, and 5b. The most potent compound (8-bromo-6-methoxy-4,5-dihydro-3H-naphtho[1,8-bc]furan-5-yl)aminomethane, 6b, had K-i values for displacement of [I-125] -DOI from 5-HT2A and 5-HT2C cloned rat receptors of 2.6 and 1.1 nM, respectively. Despite their high affinity, the compounds of this naphthofuran series lacked high intrinsic activity at the 5-HT2A receptor as measured using the phosphoinositide hydrolysis assay. The most potent compound in vitro, 6b, was tested in the two-lever drug discrimination assay in rats trained to discriminate LSD from saline, and failed to substitute, a result typical for compounds with low intrinsic activity. Thus, although conformational constraint has led to high-affinity 5-HT2A ligands with partial agonist activity, all of the spatial and steric properties of the ligand necessary for full receptor activation have not yet been identified.

  DOI：

  10.1021/jm030064v
• 作为产物：
  描述：

  4-甲氧基苯酚 在 溴 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 methyl 4-(2-bromo-4-methoxyphenoxy)but-2-enoate
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of a Series of Geometrically Constrained 5-HT_2A/2C Receptor Ligands

  摘要：

  In studies of the SAR of phenethylamine-type serotonin 5-HT2A receptor agonists, substituted conformationally constrained tetrahydronaphthofurans were designed to investigate the optimal conformation of the 2-aminoethyl moiety. These compounds were tested using in vitro assays for affinity at 5-HT1A, 5-HT2A, and 5-HT2C receptors. The benzofuran-containing analogues, 6a and 6b, had significantly higher affinity for the 5-HT receptors tested than did the benzodi-hydrofuran-containing compounds, 4a, 4b, 5a, and 5b. The most potent compound (8-bromo-6-methoxy-4,5-dihydro-3H-naphtho[1,8-bc]furan-5-yl)aminomethane, 6b, had K-i values for displacement of [I-125] -DOI from 5-HT2A and 5-HT2C cloned rat receptors of 2.6 and 1.1 nM, respectively. Despite their high affinity, the compounds of this naphthofuran series lacked high intrinsic activity at the 5-HT2A receptor as measured using the phosphoinositide hydrolysis assay. The most potent compound in vitro, 6b, was tested in the two-lever drug discrimination assay in rats trained to discriminate LSD from saline, and failed to substitute, a result typical for compounds with low intrinsic activity. Thus, although conformational constraint has led to high-affinity 5-HT2A ligands with partial agonist activity, all of the spatial and steric properties of the ligand necessary for full receptor activation have not yet been identified.

  DOI：

  10.1021/jm030064v