(1R,4R)-Δ²-tetrahydrocannabinol | 95543-62-7

• 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: (1R,4R)-Δ²-tetrahydrocannabinol
• 英文别名: (6aR,9R)-Δ¹⁰-tetrahydrocannabinol；trans-Δ¹⁰-THC；(6AR,9R)-Delta10-thc；(6aR,9R)-6,6,9-trimethyl-3-pentyl-6a,7,8,9-tetrahydrobenzo[c]chromen-1-ol
• CAS: 95543-62-7
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: YLTWYAXWDLZZCU-RHSMWYFYSA-N

物化性质

• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (1R,4R)-Δ²-tetrahydrocannabinol 在 对甲苯磺酸 作用下， 以 吡啶 、 苯 为溶剂， 反应 0.5h， 生成 (1R)-Δ3-tetrahydrocannabinol acetate
  参考文献：
  名称：

  Srebnik, Morris; Lander, Naphtali; Breuer, Aviva, Journal of the Chemical Society. Perkin transactions I, 1984, # 12, p. 2881 - 2886

  摘要：

  DOI：
• 作为产物：
  描述：

  THC-O-acetate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.0h， 生成 (1R,4R)-Δ²-tetrahydrocannabinol
  参考文献：
  名称：

  Srebnik, Morris; Lander, Naphtali; Breuer, Aviva, Journal of the Chemical Society. Perkin transactions I, 1984, # 12, p. 2881 - 2886

  摘要：

  DOI：

文献信息

• [EN] METHODS FOR PREPARING CANNABINOIDS BY BASE-PROMOTED DOUBLE-BOND MIGRATION<br/>[FR] PROCÉDÉS DE PRÉPARATION DE CANNABINOÏDES PAR MIGRATION À DOUBLE LIAISON ACTIVÉE PAR LA BASE
  申请人：CANOPY GROWTH CORP

  公开号：WO2020248059A1

  公开（公告）日：2020-12-17

  Disclosed is a method for converting a first cannabinoid into a second cannabinoid that is a regioisomer of the first cannabinoid. The method comprising contacting the first cannabinoid with: (i) a base having a pKb that is less than a critical pKb for the first cannabinoid; and (ii) a solvent system comprising a polar solvent such as dimethyl sulfoxide (DMSO), triethylamine (TEA), or a combination thereof.

  揭示了一种将第一类大麻素转化为第二类大麻素的方法，该第二类大麻素是第一类大麻素的异构体。该方法包括将第一类大麻素与以下物质接触：(i) 具有比第一类大麻素的临界pKb更小的pKb的碱；以及 (ii) 包括极性溶剂的溶剂系统，如二甲基亚砜（DMSO）、三乙胺（TEA）或二者的组合。
• [EN] IMPROVED METHODS FOR CANNABINOID ISOMERIZATION<br/>[FR] PROCÉDÉS AMÉLIORÉS D'ISOMÉRISATION DE CANNABINOÏDES
  申请人：CANOPY GROWTH CORP

  公开号：WO2020248062A1

  公开（公告）日：2020-12-17

  Disclosed herein is a method for converting a first cannabinoid into a composition comprising a second cannabinoid and a third cannabinoid, in which the second cannabinoid and the third cannabinoid are each isomers of the first cannabinoid. The composition has a second cannabinoid:third cannabinoid ratio of greater than 1.0:1.0. The method comprises contacting the first cannabinoid with a Lewis-acidic heterogeneous reagent under reaction conditions comprising: (i) a protic-solvent environment, an aprotic-solvent environment, or a solvent-free environment; (ii) a reaction temperature that is within a target reaction-temperature range for the Lewis- acidic heterogeneous reagent and the solvent/solvent free environment; and (iii) a reaction time that is within a target reaction-time range for the Lewis-acidic heterogeneous reagent, the solvent/solvent-free environment, and the reaction temperature.

  本公开涉及一种将第一大麻素转化为包含第二大麻素和第三大麻素的组合物的方法，其中第二大麻素和第三大麻素分别是第一大麻素的异构体。该组合物具有大于1.0:1.0的第二大麻素:第三大麻素比率。该方法包括将第一大麻素与Lewis酸性杂质试剂在反应条件下接触，包括：（i）具有脂溶剂环境、无水脂溶剂环境或无溶剂环境；（ii）反应温度在Lewis酸性杂质试剂和溶剂/无溶剂环境的目标反应温度范围内；（iii）反应时间在Lewis酸性杂质试剂、溶剂/无溶剂环境和反应温度的目标反应时间范围内。
• [EN] METHODS FOR CONVERTING TETRAHYDROCANNABINOLIC ACID INTO CANNABINOLIC ACID<br/>[FR] PROCÉDÉS DE CONVERSION DE L'ACIDE TÉTRAHYDROCANNABINOLIQUE EN ACIDE CANNABINOLIQUE
  申请人：CANOPY GROWTH CORP

  公开号：WO2021035342A1

  公开（公告）日：2021-03-04

  Disclosed herein is a method for converting tetrahydrocannabinolic acid (THCA) to cannabinolic acid (CBNA). The method comprises contacting an input material comprising THCA with a benzoquinone reagent under reaction conditions comprising: (i) a reaction temperature that is within a target reaction-temperature range; and (ii) a reaction time that is within a target reaction-time range, to provide an output material in which at least a portion of the THCA from the input material has been converted into CBNA.

  本文揭示了一种将四氢大麻酸（THCA）转化为大麻酸（CBNA）的方法。该方法包括将含有THCA的输入物料与苯醌试剂在反应条件下接触，所述反应条件包括：（i）反应温度在目标反应温度范围内；以及（ii）反应时间在目标反应时间范围内，从而提供输出物料，其中输入物料中的至少一部分THCA已被转化为CBNA。
• [EN] METHODS OF SYNTHESIZING HIGH-PURITY CANNABICYCLOL AND ARTIFICIAL RESINS COMPRISING CANNABICYCLOL<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE CANNABICYCLOL DE HAUTE PURETÉ ET RÉSINES ARTIFICIELLES COMPRENANT DE LA CANNABICYCLOL
  申请人：CANOPY GROWTH CORP

  公开号：WO2021127788A1

  公开（公告）日：2021-07-01

  Compositions having enhanced cannabicyclol (CBL) or CBL derivative concentrations are disclosed herein as are methods of synthesizing CBL and CBL derivative in high-purity form. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) be more tolerant of complex starting compositions, such as cannabinoid extracts, isolates and/or distillates; (iii) provide CBL and/or CBL derivative at higher yield; (iv) provide easier methods to purify product mixtures comprising CBL and/or CBL derivative; (v) provide product mixtures that comprise unique ratios of CBL or CBL derivative relative to other cannabinoids; (vi) provide product mixtures with reduced THC concentrations and/or (vii) provide artificial resins having of a mixture cannabinoids that cannot be produced by extracting cannabis plant material.

  本文披露了具有增强型大麻环酚（CBL）或CBL衍生物浓度的组合物，以及合成高纯度形式的CBL和CBL衍生物的方法。相对于传统方法，本公开的方法可能：（i）更适合于大规模条件，因为它们不需要危险和/或有毒的溶剂和/或试剂；（ii）更容忍复杂的起始组合物，如大麻提取物、分离物和/或蒸馏液；（iii）提供更高产量的CBL和/或CBL衍生物；（iv）提供更容易纯化含有CBL和/或CBL衍生物的产品混合物的方法；（v）提供相对于其他大麻素具有独特比率的CBL或CBL衍生物的产品混合物；（vi）提供具有降低THC浓度的产品混合物和/或（vii）提供具有无法通过提取大麻植物材料生产的混合大麻素的人工树脂。
• WATER-SOLUBLE FORMULATIONS, METHODS OF MAKING AND USE
  申请人：CANOPY GROWTH CORPORATION

  公开号：US20200170944A1

  公开（公告）日：2020-06-04

  Water-soluble formulations including cannabinoids or a cannabis -derived compound for use in beverages and foods, methods of preparing the formulations, and methods of preparing beverages and foods including the formulations are disclosed herein. In other embodiments are provided water-soluble formulations that are physically and chemically stable, transparent or translucent in colour, calorie-free, and have minimal flavour.