3-(1,1-dimethyl-heptyl)-1-hydroxy-9-methyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one | 61133-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(1,1-dimethyl-heptyl)-1-hydroxy-9-methyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one
• 英文别名: 3-(1,1-Dimethyl-heptyl)-1-hydroxy-9-methyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-on；1-Hydroxy-9-methyl-3-(2-methyloctan-2-yl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one；1-hydroxy-9-methyl-3-(2-methyloctan-2-yl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
• CAS: 61133-22-0
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: MXLFYAKWJFGPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1,1-dimethyl-heptyl)-1-hydroxy-9-methyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one 在 sulfur 作用下， 反应 4.0h， 以72%的产率得到3-(1,1-dimethylheptyl)-1-hydroxy-9-methyl-6H-dibenzo[b,d]pyran-6-one
  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
• 作为产物：
  描述：

  1-(1,1-二甲基庚基)-3,5-二甲氧基苯 在 氢溴酸 、 溶剂黄146 、 三氯氧磷 、 苯 作用下， 生成 3-(1,1-dimethyl-heptyl)-1-hydroxy-9-methyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one
  参考文献：
  名称：

  四氢大麻酚同系物。

  摘要：

  DOI：

  10.1021/ja01182a067

文献信息

• Tetrahydrocannabinol Homologs. XVII.¹
  作者：Roger Adams、Ben F. Aycock、S. Loewe

  DOI：10.1021/ja01182a067

  日期：1948.2
• Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase
  作者：Man-Hee Rhee、Zvi Vogel、Jacob Barg、Michael Bayewitch、Rivka Levy、Lumir Hanuš、Aviva Breuer、Raphael Mechoulam

  DOI：10.1021/jm970126f

  日期：1997.9.1

  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).