(-)-11-n-9-羧基-δ9-THC | 56354-06-4

• 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: (-)-11-n-9-羧基-δ9-THC
• 中文别名: (-)-11-9-羧基-Δ-9-四氢大麻酚
• 英文名称: 11-nor-9-carboxt-Δ-9-tetrahydrocannabinol
• 英文别名: 11-nor-9-carboxy-Δ9-tetrahydrocannabinol；1,1-nor-9-carboxy-THC；11-COOH-THC；11-Nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid；11-Nor-9-carboxy-delta-9-tetrahydrocannabinol；(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
• CAS: 56354-06-4
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: YOVRGSHRZRJTLZ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：

  N-羟基丁二酰亚胺 、 (-)-11-n-9-羧基-δ9-THC 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 2,5-dioxopyrrolidin-1-yl (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylate
  参考文献：
  名称：

  [EN] TETRAHYDROCANNABINOID- PROTEIN CONJUGATES FOR THE PRODUCTION OF ANTIBODIES FOR THE DETECTION OF T?TRAHYDROCANNABINOID COMPONENTS IN SALIVA
  [FR] ANTIGENES TETRAHYDROCANNABINOIDES ET LEUR PROCEDE D'UTILISATION

  摘要：

  公开号：

  WO2006029089A3
• 作为产物：
  描述：

  dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 在 正丁基锂 、 高氯酸 、 四甲基乙二胺 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 29.03h， 生成 (-)-11-n-9-羧基-δ9-THC
  参考文献：
  名称：

  Preparation of Racemic, (−)- and (+)-11-Nor-Δ⁹-Tetrahydrocannabinol- 9-carboxylic Acid

  摘要：

  DOI：

  10.1021/jo970969e

文献信息

• Studies on the Synthesis of (-)-11-Nor-9-carboxy-Δ⁹-Tetrahydrocannabinol (THC) and Related Compounds: An Improved Oxidative Procedure
  作者：Craig Siegel、Patrick M. Gordon、Raj K. Razdan

  DOI：10.1055/s-1991-26590

  日期：——

  A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥ 80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.

  本文介绍了一种简便的方法，即在大量过量的 2-甲基-2-丁烯存在下，用亚氯酸钠将δ9-四氢大麻酚醛 4 及其叔丁基二甲基硅烷衍生物方便地氧化成相应的酸，而不会发生δ9-双键的异构化。 在四氢呋喃中用四丁基氟化铵对 O 保护基进行脱保护处理，得到酸 2，总收率≥80%。对其他氧化剂和保护基团的研究表明，这是制备 9-羧基-δ9-四氢大麻酚的首选方法。
• A convenient synthesis of (–)-11-nor-Δ⁹-tetrahydrocannabinol-9-methanol
  作者：Marcus A. Tius、Xue-qin Gu、Michael A. Kerr

  DOI：10.1039/c39890000062

  日期：——

  A convenient enantiospecific total synthesis of (–)-11-nor-Δ9-tetrahydrocannabinol-9-methanol, a human urinary metabolite of Δ9-tetrahydrocannabinol, has been accomplished in six steps from (R)-(+)-perillaldehyde.

  (R)-(+ )-紫苏醛。
• Cannabinoid active pharmaceutical ingredient for improved dosage forms
  申请人：Kupper J. Robert

  公开号：US20070072939A1

  公开（公告）日：2007-03-29

  Pharmaceutical compositions comprising the cannabinoid active pharmaceutical ingredient, crystalline trans-(±)-Δ 9 -tetrahydrocannabinol, and formulations thereof are disclosed. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of crystalline trans-(±)-Δ 9 -tetrahydrocannabinol. In specific embodiments, the crystalline trans-(±)-Δ 9 -tetrahydrocannabinol administered according to the methods for treating or preventing a condition such as pain can have a purity of at least about 98% based on the total weight of cannabinoids.

  本发明揭示了含有大麻活性药物成分晶态转化物-(±)-Δ9-四氢大麻酚及其制剂的制药组合物。本发明还涉及一种治疗或预防疼痛等病症的方法，包括向需要治疗的患者投与有效量的晶态转化物-(±)-Δ9-四氢大麻酚。在具体实施例中，根据治疗或预防疼痛等病症的方法投与的晶态转化物-(±)-Δ9-四氢大麻酚，其纯度可以基于大麻素的总重量而至少达到约98%。
• Methods For Purifying Trans-(-) Delta9-Tetrahydrocannabinol And Trans-(+)-Delta9-Tetrahydrocannabinol
  申请人：Gutman Arie L.

  公开号：US20090298930A1

  公开（公告）日：2009-12-03

  Methods for making trans-(−)-Δ 9 -tetrahydrocannabinol and trans-(+)-Δ 9 -tetrahydrocannabinol are disclosed herein. In one embodiment, a trans-(−)-Δ 9 -tetrahydrocannabinol composition is prepared by allowing a composition comprising (±)-Δ 9 -tetrahydrocannabinol to separate on a chiral stationary phase to provide a trans-(−)-Δ 9 -tetrahydrocannabinol composition comprising at least about 99% by weight of trans-(−)-Δ 9 -tetrahydrocannabinol based on the total amount of trans-(−)-Δ 9 -tetrahydrocannabinol and trans-(+)-Δ 9 -tetrahydrocannabinol. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of a trans-(−)-Δ 9 -tetrahydrocannabinol having a purity of at least about 98% based on the total weight of cannabinoids.

  本文披露了制备反式-(−)-Δ9-四氢大麻酚和反式-(+)-Δ9-四氢大麻酚的方法。在一种实施方式中，通过让包含(±)-Δ9-四氢大麻酚的组合物在手性固定相上分离，制备了一种反式-(−)-Δ9-四氢大麻酚组合物，其中反式-(−)-Δ9-四氢大麻酚的重量占反式-(−)-Δ9-四氢大麻酚和反式-(+)-Δ9-四氢大麻酚总量的至少约99%。本发明还涉及治疗或预防疼痛等病症的方法，包括向需要的患者施用至少98%纯度的反式-(−)-Δ9-四氢大麻酚的有效剂量，基于大麻素的总重量。
• METHODS FOR PURIFYING TRANS-(-)-DELTA9-TETRAHYDROCANNABINOL AND TRANS-(+)-DELTA9-TETRAHYDROCANNABINOL
  申请人：Purdue Pharma L.P.

  公开号：US20130171259A1

  公开（公告）日：2013-07-04

  Methods for making trans-(−)-Δ 9 -tetrahydrocannabinol and trans-(+)-Δ 9 -tetrahydrocannabinol are disclosed herein. In one embodiment, a trans-(−)-Δ 9 -tetrahydrocannabinol composition is prepared by allowing a composition comprising (±)-Δ 9 )-tetrahydrocannabinol to separate on a chiral stationary phase to provide a trans-(−)-Δ 9 -tetrahydrocannabinol composition comprising at least about 99% by weight of trans-(−)-Δ 9 -tetrahydrocannabinol based on the total amount of trans-(−)-Δ 9 -tetrahydrocannabinol and trans-(+)-Δ 9 -tetrahydrocannabinol. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of a trans-(−)-Δ 9 -tetrahydrocannabinol having a purity of at least about 98% based on the total weight of cannabinoids.

  本文公开了制备反式-(−)-Δ9-四氢大麻酚和反式-(+)-Δ9-四氢大麻酚的方法。在一种实施例中，通过让包含(±)-Δ9-四氢大麻酚的组成物在手性固定相上分离，制备出反式-(−)-Δ9-四氢大麻酚组成物，其中反式-(−)-Δ9-四氢大麻酚的重量占反式-(−)-Δ9-四氢大麻酚和反式-(+)-Δ9-四氢大麻酚总量的至少约99%。本发明还涉及治疗或预防疼痛等疾病的方法，包括向需要治疗的患者投与至少约98%纯度的反式-(−)-Δ9-四氢大麻酚，其基于大麻素总重量计算。