(4R)-4-(4-pentyl-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone | 145104-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-4-(4-pentyl-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone
• 英文别名: (1R,4R,5R)-4-(2,6-dihydroxy-4-pentylphenyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-one
• CAS: 145104-69-4
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: ROVVOYDQNXKGHL-KFWWJZLASA-N

物化性质

• 熔点：
  141-143 °C(Solvent: Dichloromethane; Hexane)
• 沸点：
  482.8±24.0 °C(predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-(4-pentyl-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone 在 四氯化锡 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以72%的产率得到dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on
  参考文献：
  名称：

  （ - 5'合成2 ħ 3） - （ - ） - 11-NOR -9-羧基- Δ 9 -四氢大麻酚甲酯甲基醚

  摘要：

  的5'的合成- （2 ħ 3） - （ - ） - 11-NOR -9-羧基- Δ 9 -四氢大麻酚甲酯甲基醚（4）已被从α-bromoenone完成10。的关键步骤是铜酸盐加成物的立体控制环丁烷环开口18和环己烯基三氟甲磺酸酯的环化21用过量的三甲基碘硅烷，以产生Δ 9环己烯基三氟甲磺酸酯22。还已经完成了光学活性的（-）-d11-nor-9-酮-六氢大麻酚（8）的高效立体定向合成。

  DOI：

  10.1016/s0040-4020(01)85608-8
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 84.0h， 以7 mg的产率得到(4R)-4-(4-pentyl-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone
  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

文献信息

• Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity
  作者：Marcus A. Tius、Alexandros Makriyannis、Xiang Long Zoua、V. Abadji

  DOI：10.1016/s0040-4020(01)86983-0

  日期：1994.2

  A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (-)-9-nor-9 beta-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6 during the key step is accomplished through an intramolecular oxymercuration reaction. The prediction that the analogs would exhibit different degrees of binding to the cannabinoid receptor was borne out. This observation sheds light on the stereochemical requirements of the receptor.
• TIUS, MARCUS A.;KANNANGARA, G. S. KAMALI, J. ORG. CHEM., 55,(1990) N2, C. 5711-5714
  作者：TIUS, MARCUS A.、KANNANGARA, G. S. KAMALI

  DOI：——

  日期：——
• A concise methodology for the synthesis of (−)-Δ9-tetrahydrocannabinol and (−)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs
  作者：Spyros P. Nikas、Ganesh A. Thakur、Damon Parrish、Shakiru O. Alapafuja、Marilyn A. Huestis、Alexandros Makriyannis

  DOI：10.1016/j.tet.2007.06.006

  日期：2007.8

  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.
• Synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether
  作者：Marcus A. Tius、G.S.Kamali Kannangara

  DOI：10.1016/s0040-4020(01)85608-8

  日期：1992.1

  A synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether (4) has been accomplished from α-bromoenone 10. The key steps are the stereocontrolled cyclobutane ring opening of the cuprate adduct 18 and the cyclization of the cyclohexenyl triflate 21 with excess iodotrimethylsilane to produce Δ9-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically

  的5'的合成- （2 ħ 3） - （ - ） - 11-NOR -9-羧基- Δ 9 -四氢大麻酚甲酯甲基醚（4）已被从α-bromoenone完成10。的关键步骤是铜酸盐加成物的立体控制环丁烷环开口18和环己烯基三氟甲磺酸酯的环化21用过量的三甲基碘硅烷，以产生Δ 9环己烯基三氟甲磺酸酯22。还已经完成了光学活性的（-）-d11-nor-9-酮-六氢大麻酚（8）的高效立体定向合成。