四氢大麻酚-7-酸 | 39690-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 四氢大麻酚-7-酸
• 中文别名: 9-羧基-11-去甲基-Δ8-四氢大麻酚；9-羧基-11-去甲基-&Delta8-四氢大麻酚
• 英文名称: Δ⁸-THC-11-oic acid
• 英文别名: Δ⁸-tetrahydrocannabinol-11-oic acid；Δ6-tetrahydrocannabinol-7-oic acid；11-nor-9-carboxy-A9-THC；D8-THC-11-oic acid；(6aR,10aR)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic acid；delta(8)-Thc-11-oic acid；(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
• CAS: 39690-06-7
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: OGXXAQFMAFTSRU-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  四氢大麻酚-7-酸 、 (trans-rac)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo(b,d)pyran-9-carboxylic Acid Methyl Ester 、 在 氩 、 sodium hydroxide 、 甲醇 、 hexanes-CHCl3 MeOH 、 氯仿 作用下， 反应 18.0h， 以to give, from the main band, 16 mg, 76%, of the (6aS,10aS)-acid (XVIII) as a glass, [α]D +310° (CHCl3), M+ 344.1983 (Calc 344.1988)的产率得到11-nor-Δ⁸tetrahydrocannabinol-9-carboxylic acid
  参考文献：
  名称：

  Compounds having improved fluorescence in fluorescence polarization

  摘要：

  分子式为##STR1##的化合物，其中F是荧光化合物；Y是--NH--或单个共价键；Z是2至10个碳原子的直链或支链烷基链，其被至少一个亲水基团取代；Q是氧或硫；X是配体类似物，该配体类似物能够被特异性抗体识别。这些化合物在荧光偏振免疫测定中具有改进的性质，因为它们具有更好的强度和/或更大的跨度。

  公开号：

  US05315015A1
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 四氢大麻酚-7-酸
  参考文献：
  名称：

  大麻素代谢物的合成：Ajulemic Acid 和 胡-210

  摘要：

  据报道，大麻素代谢物比其母体化合物更有效。其中，ajulemic acid （AJA） 是 Δ9-THC-11-oic acid 的侧链类似物，这将是发现更有效类似物的良好模板结构。在此，我们优化了关键的烯丙基氧化步骤，以高产率引入 C-11 羟基。在此条件下制备了一系列化合物，包括 胡-210、11-nor-Δ8-四氢大麻酚 （THC）-羧酸和 Δ9-THC-羧酸。

  DOI：

  10.3390/molecules29020526

文献信息

• Compounds for fluoroscense polarization immunoassays and immunoassays utilising them
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0597333A2

  公开（公告）日：1994-05-18

  Compounds of the formula wherein F is a fluorescing compound; Y is -NH- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.

  式中的化合物 其中 F 是荧光化合物；Y 是-NH-或单个共价键；Z 是 2 至 10 个碳原子的直链或支链亚烷基链，至少被一个亲水基团取代；Q 是氧或硫；X 是配体类似物，配体类似物能够被相应配体的特异性抗体识别。这些化合物具有更好的强度和/或更大的跨度，从而改善了荧光偏振免疫分析的性能。
• 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.
• Convenient synthesis of 11-nor-.DELTA.8-tetrahydrocannabinol-9-carboxylic acid
  作者：Alan Schwartz、Pradeep Madan

  DOI：10.1021/jo00376a090

  日期：1986.12
• US5315015A
  申请人：——

  公开号：US5315015A

  公开（公告）日：1994-05-24
• Compounds having improved fluorescence in fluorescence polarization
  申请人：Hoffmann-La Roche Inc.

  公开号：US05315015A1

  公开（公告）日：1994-05-24

  Compounds of the formula ##STR1## wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.

  分子式为##STR1##的化合物，其中F是荧光化合物；Y是--NH--或单个共价键；Z是2至10个碳原子的直链或支链烷基链，其被至少一个亲水基团取代；Q是氧或硫；X是配体类似物，该配体类似物能够被特异性抗体识别。这些化合物在荧光偏振免疫测定中具有改进的性质，因为它们具有更好的强度和/或更大的跨度。