2β-hydroxyhexahydrocannabinol | 60948-21-2

• 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: 2β-hydroxyhexahydrocannabinol
• 英文别名: 10(R)-hydroxy-9(S)-Hexahydrocannabinol；(6aR,9S,10R,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,10-diol
• CAS: 60948-21-2
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: SUVXTOCRTNYFMQ-ASCUOWJESA-N

物化性质

• 沸点：
  426.6±45.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2β-hydroxyhexahydrocannabinol 在 吡啶 作用下， 生成 Acetic acid (6aR,9S,10R,10aR)-1-acetoxy-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-10-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：

  (6aR,10aalpha)-6abeta,7,8,10alpha-四氢-6,6,9-三甲基-3-戊基-6H-二苯并[b,d]吡喃-1-醇乙酸酯 在 sodium hydroxide 、 双氧水 、 diborane(6) 作用下， 生成 2β-hydroxyhexahydrocannabinol 、 2α-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