1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene | 58545-61-2

• 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-[5'-(2H3)-pentyl]benzene
• 英文别名: 5'-2H3-olivetol；Olivetol-5'-D3；5-(5,5,5-Trideuteriopentyl)benzene-1,3-diol
• CAS: 58545-61-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 183.223
• InChiKey: IRMPFYJSHJGOPE-FIBGUPNXSA-N

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：

  1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene 、 反式-薄荷基-2,8-二烯-1-醇 在 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到6α,7,8,10α-四氢-6,6,9-三甲基-3-(戊基-5,5,5-D3)-6H-二苯并[B,D]吡喃-1-醇
  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：

  4-(3,5-dimethoxyphenyl)-1-butanol 在 dilithium tetrachlorocuprate 三甲基氯硅烷 、 碘代三甲硅烷 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 乙腈 为溶剂， 反应 76.0h， 生成 1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene
  参考文献：
  名称：

  Girard, Michel; Moir, David B.; Apsimon, John W., Canadian Journal of Chemistry, 1987, vol. 65, p. 189 - 190

  摘要：

  DOI：

文献信息

• The synthesis of deuterium, carbon-14, and carrier-free tritium labeled cannabinoids
  作者：C. G. Pitt、D. T. Hobbs、H. Schran、C. E. Twine、D. L. Williams

  DOI：10.1002/jlcr.2590110412

  日期：——

  1′,2′-Dehydroolivetol and its monomethyl ether, 5′-bromoolivetol, and olivetol-5,-2H3, have been synthesized. Acid catalyzed condensation of the latter three compounds with p-mentha-2,8-dien-1-ol gave 1′,2′-dehydro-Δ8-THC methyl ether, 5′-bromo-Δ8-THC, and Δ9-THC-5′-2H3, respectively. 5′-Bromo-Δ8-THC served as a precursor of 4′,5′-dehydro-Δ8- and Δ8-THC, 4′- and 5′-hydroxy-Δ8-THC, 5′-dimethylamino-Δ8-THC and 5′-carboxy-Δ8-THC. Reduction of 4′,5′-dehydro-Δ8- and Δ9-THC in the presence of homogeneous catalysts afforded tritium labeled Δ8-THC (50 Ci/mmole) and Δ9-THC (58 Ci/mmole), respectively. Syntheses of Δ9-THC-11-2H3, Δ9-THC-11-14C cannabinol-5,-2H3′ and other labeled cannabinoids are described.

  1′,2′-Dehydroolivetol 及其单甲醚、5′-bromoolivetol 和 olivetol-5,-2H3已被合成。在酸催化下，后三种化合物与对薄荷-2,8-二烯-1-醇缩合，分别得到 1′,2′-脱氢-Δ8-THC 甲醚、5′-溴-Δ8-THC 和 Δ9-THC-5′-2H3。5′-Bromo-Δ8-THC 是 4′、5′-脱氢-Δ8-和Δ8-THC、4′-和 5′-羟基-Δ8-THC、5′-二甲氨基-Δ8-THC 和 5′-羧基-Δ8-THC 的前体。在均相催化剂存在下还原 4′,5′-脱氢-Δ8-和 Δ9-THC，分别得到氚标记的 Δ8-THC（50 Ci/mmole）和 Δ9-THC（58 Ci/mmole）。介绍了Δ9-THC-11-2H3、Δ9-THC-11-14C 大麻酚-5,-2H3′ 和其他标记大麻素的合成。
• 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.