1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene | 504396-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene
• 英文别名: 5-(4,4,5,5,5-Pentadeuteriopentyl)benzene-1,3-diol
• CAS: 504396-87-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 185.207
• InChiKey: IRMPFYJSHJGOPE-ZBJDZAJPSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  313.259±12.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.069±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-薄荷基-2,8-二烯-1-醇 、 1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene 在 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以29%的产率得到4'-(2H2)-5'-(2H3)-Δ⁹-tetrahydrocannabiol
  参考文献：
  名称：

  Synthesis of side chain specifically deuterated (?)-?9-tetrahydrocannabinols

  摘要：

  (以相应的间苯二酚为关键中间体，制备了在正戊基侧链上特异性氚化的（-）-Δ9-四氢大麻酚。为了获得氚代间苯二酚，我们开发了不会出现氚扰乱或损失的条件。该方法可实现氘代间苯二酚和相应的 (-)-Δ9- 四氢大麻酚的制备级合成。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.626
• 作为产物：
  描述：

  1,3-dimethoxy-5-[3'-(methanesulfonyloxy)-4'-(2H2)-5'-(2H3)-pentyl]benzene 在 三溴化硼 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene
  参考文献：
  名称：

  Synthesis of side chain specifically deuterated (?)-?9-tetrahydrocannabinols

  摘要：

  (以相应的间苯二酚为关键中间体，制备了在正戊基侧链上特异性氚化的（-）-Δ9-四氢大麻酚。为了获得氚代间苯二酚，我们开发了不会出现氚扰乱或损失的条件。该方法可实现氘代间苯二酚和相应的 (-)-Δ9- 四氢大麻酚的制备级合成。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.626

文献信息

• 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 side chain specifically deuterated (?)-?9-tetrahydrocannabinols
  作者：Spyros P. Nikas、Ganesh A. Thakur、Alexandros Makriyannis

  DOI：10.1002/jlcr.626

  日期：2002.10.30

  (−)-Δ9-Tetrahydrocannabinols specifically deuterated at the n-pentyl side chain were prepared using the corresponding resorcinols as key intermediates. To obtain the deuterated resorcinols we developed conditions under which no deuterium scrambling or loss was observed. The methodology allows for the preparative scale synthesis of deuterated resorcinols and corresponding (−)-Δ9-tetrahydrocannabinols. Copyright © 2002 John Wiley & Sons, Ltd.

  (以相应的间苯二酚为关键中间体，制备了在正戊基侧链上特异性氚化的（-）-Δ9-四氢大麻酚。为了获得氚代间苯二酚，我们开发了不会出现氚扰乱或损失的条件。该方法可实现氘代间苯二酚和相应的 (-)-Δ9- 四氢大麻酚的制备级合成。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.