7-(cyclohexylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one | 1287785-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-(cyclohexylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one
• 英文别名: 7-(cyclohexylmethylidene)-2,6-dihydro-1H-cyclopenta[e][1]benzofuran-8-one
• CAS: 1287785-35-6
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: PGDMSRUOXNMFAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-(cyclohexylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以77%的产率得到7-(cyclohexylmethyl)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one
  参考文献：
  名称：

  1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists

  摘要：

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.

  DOI：

  10.1021/jm200221q
• 作为产物：
  描述：

  环己烷基甲醛 、 1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-酮 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以71%的产率得到7-(cyclohexylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one
  参考文献：
  名称：

  1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists

  摘要：

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.

  DOI：

  10.1021/jm200221q