(6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-2H5-pentyl)-9H-dibenzo[b,d]pyran-9-one | 949595-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-2H5-pentyl)-9H-dibenzo[b,d]pyran-9-one
• 英文别名: (6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-²H₅-pentyl)-9H-dibenzo[b,d]pyran-9-one
• CAS: 949595-90-8
• 化学式: C₂₀H₂₈O₃
• 分子量: 321.401
• InChiKey: YHIZWEDKQCYPIV-ZHVUPNNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-2H5-pentyl)-9H-dibenzo[b,d]pyran-9-one 在 正丁基锂 、 四甲基乙二胺 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 2.67h， 生成 (6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-²H₅-pentyl)-6H-dibenzo[b,d]pyran-9-methanol
  参考文献：
  名称：

  A concise methodology for the synthesis of (−)-Δ9-tetrahydrocannabinol and (−)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

  摘要：

  The availability of tetrahydrocannabinols (Delta(9)-THC), tetrahydrocannabivarins (Delta(9)-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Delta(9)-THC and (-)-Delta(9)-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Delta(9)-THC and (-)-Delta(9)-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.06.006
• 作为产物：
  描述：

  (4R)-4-[4-(4',4',5',5',5'-²H₅-pentyl)-2,6-dihydroxyphenyl]-6,6-dimethyl-2-norpinanone 在 三氟甲磺酸三甲基硅酯 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到(6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-2H5-pentyl)-9H-dibenzo[b,d]pyran-9-one
  参考文献：
  名称：

  A concise methodology for the synthesis of (−)-Δ9-tetrahydrocannabinol and (−)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

  摘要：

  The availability of tetrahydrocannabinols (Delta(9)-THC), tetrahydrocannabivarins (Delta(9)-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Delta(9)-THC and (-)-Delta(9)-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Delta(9)-THC and (-)-Delta(9)-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.06.006