1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid | 53989-32-5

• 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: 1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid
• 英文别名: Cannabinol-7-carbonsaeure；1-Hydroxy-6,6-dimethyl-3-pentyl-6H-benzo[c]chromene-9-carboxylic acid；1-hydroxy-6,6-dimethyl-3-pentylbenzo[c]chromene-9-carboxylic acid
• CAS: 53989-32-5
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: RUDAUXBQLBAKOW-UHFFFAOYSA-N

物化性质

• 沸点：
  546.4±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以92%的产率得到9-(羟基甲基)-6,6-二甲基-3-戊基苯并[c]苯并吡喃-1-醇
  参考文献：
  名称：

  Novak, Jiri; Salemink, Cornelis A., Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2867 - 2871

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Acetoxy-6,6-dimethyl-3-pentyl-6H-benzo[c]chromene-9-carboxylic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以82%的产率得到1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carboxylic acid
  参考文献：
  名称：

  Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase

  摘要：

  Several derivatives of cannabinol anti the 1,1-dimethylheptyl homolog (DMM) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K-i values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 mu M. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K-i values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).

  DOI：

  10.1021/jm970126f