(S)-4'-acetoxyolivetol | 189358-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-4'-acetoxyolivetol
• 英文别名: [(2S)-5-(3,5-dihydroxyphenyl)pentan-2-yl] acetate
• CAS: 189358-20-1
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: UXWJXNCVEAPBIG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-Δ²-p-menthene-1,8-diol 、 (S)-4'-acetoxyolivetol 在 potassium carbonate 、 zinc(II) chloride 作用下， 生成 (6aR)-3-[(4S)-4-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol 、 (6aR)-3-[(4R)-4-hydroxypentyl]-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
  参考文献：
  名称：

  Synthesis and pharmacology of (R)- and (5)-4′-hydroxy-Δ9-tetrahydrocannabinols

  摘要：

  The (R)- and (S)-4'-hydroxy-Delta(9)-tetrahydrocannabinols 1a,b (tetrahydrocannabinol = THC) were synthesized by the condensation of (+)-cis-p-menth-2-ene-1,8-diol 3 with the corresponding (R)- and (S)-4'-acetoxy olivetols 4a,b, followed by base hydrolysis. The optical purity of 1a,b was estimated to be >87% ee. Pharmacological data presented here indicate that 1a is two to three times more potent than 1b in vivo (locomotion, antinociception and catalepsy measures) and eight times more potent in its affinity for the cannabinoid CB1 receptor. Additionally, data from catalepsy and hypothermia measures at both the normal and short time-course evaluations indicate that both isomers possess a short duration of action which is presumably due to rapid metabolism. A comparison of the biological activity of 3'- and 4'-hydroxy-Delta(9)-THCs indicates that although similar specificity resides in both the 3'- and 4'-positions, the 3'-position is more important than the 4'-position since (S)-3'-hydroxy-Delta(9)-THC is much more potent than (R)-4'-hydroxy-Delta(9)-THC. Furthermore 1b has an indication of a lead for separation of hypothermic effects from other pharmacological activities.

  DOI：

  10.1016/s0223-5234(97)87544-7
• 作为产物：
  描述：

  3,5-bis(tert-butyldimethylsilyloxy)benzyl bromide 在 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 镍 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 (S)-4'-acetoxyolivetol
  参考文献：
  名称：

  Synthesis of (R)- and (S)-4′-Acetoxyolivetol [(R)- and (S)-5-(4′-Acetoxypentyl)-1, 3-benzenediol]: Key Intermediates in the Synthesis of Tetrahydrocannabinol Derivatives

  摘要：

  本研究描述了从 3,5-二羟基苯甲酸（4）合成四氢大麻酚衍生物的关键中间体 (R)- 和 (S)-4′-acetoxyolivetols 的合成过程。3,5-二羟基作为其叔丁基二甲基硅烷衍生物受到保护，苯甲酸基则转化为苄基-1,3-二噻烷衍生物 8。 将 8 的阴离子与手性 1,2-环氧丙烷处理后得到二噻烷醇 9，经过乙酰化、脱硫和酚羟基脱保护后，得到所需的 4′-乙酰氧基橄榄醇 (2a,b)，总产率为 13%。

  DOI：

  10.1055/s-1994-25509