7-hydroxyhexahydrocannabinol | 74523-47-0

• 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: 7-hydroxyhexahydrocannabinol
• 英文别名: 11-hydroxy-9(S)-Hexahydrocannabinol；(6aR,9S,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
• CAS: 74523-47-0
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: LXSFNMQURHTPIT-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7-hydroxyhexahydrocannabinol 在 吡啶 作用下， 生成 Acetic acid (6aR,9S,10aR)-9-acetoxymethyl-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-yl ester
  参考文献：
  名称：

  Stereochemical requirements for cannabinoid activity

  摘要：

  Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.

  DOI：

  10.1021/jm00184a002
• 作为产物：
  描述：

  Δ⁶-tetrahydrocannabinol-7-oic acid methyl ester acetate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 7-hydroxyhexahydrocannabinol
  参考文献：
  名称：

  Stereochemical requirements for cannabinoid activity

  摘要：

  Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.

  DOI：

  10.1021/jm00184a002