10-Methoxy-8-methyl-3,4,4a,5-tetrahydro-2H-<1>benzopyrano<3,4-b>pyridine | 118715-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 10-Methoxy-8-methyl-3,4,4a,5-tetrahydro-2H-<1>benzopyrano<3,4-b>pyridine
• 英文别名: 10-Methoxy-8-methyl-3,4,4a,5-tetrahydro-2H-[1]benzopyrano[3,4-b]pyridine；10-methoxy-8-methyl-3,4,4a,5-tetrahydro-2H-chromeno[3,4-b]pyridine
• CAS: 118715-86-9
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: RAWSUEBHUQODSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  10-Methoxy-8-methyl-3,4,4a,5-tetrahydro-2H-<1>benzopyrano<3,4-b>pyridine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 9.5h， 生成 trans-10-Methoxy-8-methyl-4-propyl-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：

  3-methoxy-5-methylphenyl 2-propynyl ether 在 正丁基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 10-Methoxy-8-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