9-Hydroxy-4-methyl-3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridine | 100745-52-6

• 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-Hydroxy-4-methyl-3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridine
• 英文别名: 4-Methyl-2,3,4a,5-tetrahydrochromeno[3,4-b]pyridin-9-ol
• CAS: 100745-52-6
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: BGBULBPIVTWFIU-UHFFFAOYSA-N

物化性质

• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-Hydroxy-4-methyl-3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 trans-9-Hydroxy-4-methyl-1,3,4,4a,5,10b-hexahydro-2H-<1>benzopyrano<3,4-b>pyridine 、 cis-9-Hydroxy-4-methyl-1,3,4,4a,5,10b-hexahydro-2H-<1>benzopyrano<3,4-b>pyridine
  参考文献：
  名称：

  2H-[1]Benzopyrano[3,4-b]pyridines. Synthesis and activity at central monoamine receptors

  摘要：

  Two general synthetic approaches to a novel series of 2H-[1]benzopyrano[3,4-b]pyridines are described together with their receptor binding profile at a variety of monoamine receptors in mammalian brain tissue. The biologically active members of this series fall into into one of two broad classes: 3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridines or trans-1,3,4,4a,5,10b-hexahydro-2H-[1]benzopyrano[3,4-b]pyridines. By appropriate pharmacophoric modification potent selective ligands for D2, alpha-2, 5HT1A, and 5HT2 receptors may be obtained. The previously published in vivo data on certain key representatives of these series are also summarized.

  DOI：

  10.1021/jm00123a039
• 作为产物：
  描述：

  9-Methoxy-3,4,4a,5-tetrahydro-2H-<1>benzopyrano<3,4-b>pyridine Hydrochloride 在 lithium aluminium tetrahydride 、 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 9-Hydroxy-4-methyl-3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridine
  参考文献：
  名称：

  2H-[1]Benzopyrano[3,4-b]pyridines. Synthesis and activity at central monoamine receptors

  摘要：

  Two general synthetic approaches to a novel series of 2H-[1]benzopyrano[3,4-b]pyridines are described together with their receptor binding profile at a variety of monoamine receptors in mammalian brain tissue. The biologically active members of this series fall into into one of two broad classes: 3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridines or trans-1,3,4,4a,5,10b-hexahydro-2H-[1]benzopyrano[3,4-b]pyridines. By appropriate pharmacophoric modification potent selective ligands for D2, alpha-2, 5HT1A, and 5HT2 receptors may be obtained. The previously published in vivo data on certain key representatives of these series are also summarized.

  DOI：

  10.1021/jm00123a039

文献信息

• 2H-[1]Benzopyrano[3,4-b]pyridines. Synthesis and activity at central monoamine receptors
  作者：Alan Hutchison、Michael Williams、Reynalda De Jesus、George A. Stone、L. Sylvester、Frank H. Clarke、Matthew A. Sills

  DOI：10.1021/jm00123a039

  日期：1989.3

  Two general synthetic approaches to a novel series of 2H-[1]benzopyrano[3,4-b]pyridines are described together with their receptor binding profile at a variety of monoamine receptors in mammalian brain tissue. The biologically active members of this series fall into into one of two broad classes: 3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridines or trans-1,3,4,4a,5,10b-hexahydro-2H-[1]benzopyrano[3,4-b]pyridines. By appropriate pharmacophoric modification potent selective ligands for D2, alpha-2, 5HT1A, and 5HT2 receptors may be obtained. The previously published in vivo data on certain key representatives of these series are also summarized.