1-Hydroxy-3,6,6,9-tetramethyl-Δ⁸-6a,10a-trans-tetrahydro-6H-dibenzopyran | 22972-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-Hydroxy-3,6,6,9-tetramethyl-Δ⁸-6a,10a-trans-tetrahydro-6H-dibenzopyran
• 英文别名: 1-Hydroxy-3,6,6,9-tetramethyl-Δ⁸-6a,10a-trans-tetrahydro-6H-dibenzo[b,d]pyran；Delta8-Tetrahydrocannabiorcol；(6aR,10aR)-3,6,6,9-tetramethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 22972-64-1
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: MMZAEMNNHWYQKW-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-3,6,6,9-tetramethyl-Δ⁸-6a,10a-trans-tetrahydro-6H-dibenzopyran 在 哌啶乙酸盐 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 22.0h， 生成 5,8,8,11-Tetramethyl-8a,9,12,12a-tetrahydro-1H-(2)-benzopyrano<3,4-h>cumarin-3-yl-carbonsaeuremethylester
  参考文献：
  名称：

  甲酰基-四氢大麻酚衍生物的制备与反应

  摘要：

  四氢大麻酚衍生物 3a、3b 和 17 与 Vilsmeier 试剂反应生成醛 4a、4d、5a、5b、18 和 19。这些与 CH-酸性化合物缩合生成吡喃-THC 衍生物 6a、6b、6d、6e， 8、10 和 20。

  DOI：

  10.1002/ardp.19823150613
• 作为产物：
  描述：

  3,5-二羟基甲苯 、 反式-薄荷基-2,8-二烯-1-醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以22%的产率得到1-Hydroxy-3,6,6,9-tetramethyl-Δ⁸-6a,10a-trans-tetrahydro-6H-dibenzopyran
  参考文献：
  名称：

  甲酰基-四氢大麻酚衍生物的制备与反应

  摘要：

  四氢大麻酚衍生物 3a、3b 和 17 与 Vilsmeier 试剂反应生成醛 4a、4d、5a、5b、18 和 19。这些与 CH-酸性化合物缩合生成吡喃-THC 衍生物 6a、6b、6d、6e， 8、10 和 20。

  DOI：

  10.1002/ardp.19823150613

文献信息

• Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-<i>ortho</i> -Tetrahydrocannabinols and Analogues from Natural Feedstocks
  作者：Pascal D. Giorgi、Virginie Liautard、Mathieu Pucheault、Sylvain Antoniotti

  DOI：10.1002/ejoc.201800064

  日期：2018.3.22

  A short synthesis of (±)‐tetrahydrocannabinol derivatives is described. This method relies on the oxidation of natural terpenyl alcohols by gold nanoparticles under O2 followed by original condensation with resorcinol derivatives catalyzed by TiIV supported on montmorillonite with unusual regioselectivity to access ortho‐tetrahydrocannabinol structures.

  描述了（±）-四氢大麻酚衍生物的简短合成。该方法依赖于金纳米颗粒在O 2下将天然萜烯醇氧化，然后与负载在蒙脱石上的Ti IV催化的间苯二酚衍生物进行原始缩合，并具有不寻常的区域选择性，从而可进入邻四氢大麻酚结构。
• 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。
• METHODS FOR PURIFYING TRANS-(-)-Delta9-TETRAHYDROCANNABINOL AND TRANS-(+)-Delta9-TETRAHYDROCANNABINOL
  申请人：SVC Pharma LP

  公开号：US20150126596A1

  公开（公告）日：2015-05-07

  Methods for making trans-(−)-Δ 9 -tetrahydrocannabinoI and trans-(+)-Δ 9 -tetrahydrocannabinol are disclosed herein. In one embodiment, a trans-(−)-Δ 9 -tetrahydrocannabinoI composition is prepared by allowing a composition comprising (±)-Δ 9 -tetrahydrocannabinol to separate on a chiral stationary phase to provide a trans-(−)-Δ 9 -tetrahydrocannabinoI 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 -tetrahydrocannabinoI 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。在一种实施例中，通过让包含(±)-Δ9-四氢大麻酚的组合物在手性固定相上分离，制备出含有至少约99%按重量计的反式-(−)-Δ9-四氢大麻酚的组合物，基于反式-(−)-Δ9-四氢大麻酚和反式-(+)-Δ9-四氢大麻酚的总量。本发明还涉及用含有至少约98%按重量计的大麻素总量的反式-(−)-Δ9-四氢大麻酚的有效量，治疗或预防疼痛等病症的方法。