6a,7,8,10a-四氢-1-羟基-6,6-二甲基-3-戊基-6H-二苯并(b,d)吡喃-9-甲醇 | 36557-05-8

• 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: 6a,7,8,10a-四氢-1-羟基-6,6-二甲基-3-戊基-6H-二苯并(b,d)吡喃-9-甲醇
• 中文别名: 11-羟基-Δ9-四氢大麻酚；11-羟基-&Delta9-四氢大麻酚
• 英文名称: 11-hydroxy-Δ⁹-6a,10a-trans-tetrahydrocannabinol
• 英文别名: (+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol；(-)-11-hydroxy-Δ⁹-tetrahydrocannabinol；11-hydroxy-6a,10a-trans-Δ⁹-THC；(+/-)-11-hydroxy-Δ9-tetrahydrocannabinol；11-Hydroxytetrahydrocannabinol；(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 36557-05-8
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: YCBKSSAWEUDACY-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

11-羟基-四氢大麻酚是已知的大麻素delta-9-四氢大麻酚的人类代谢物。

11-hydroxy-delata-Tetrahydrocannabinol is a known human metabolite of delta-9-Tetrahydrocannabinol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  (+)-紫苏醛 在 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢氟酸 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.25h， 生成 6a,7,8,10a-四氢-1-羟基-6,6-二甲基-3-戊基-6H-二苯并(b,d)吡喃-9-甲醇
  参考文献：
  名称：

  Synthesis of racemic and optically active .DELTA.9-tetrahydrocannabinol (THC) metabolites

  摘要：

  The preparation of racemic and optically active DELTA-9-THC metabolites is described from synthon 13. Racemic synthon 13 is prepared in four steps (46%) from Danishefsky's diene. Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23% yield). Alternatively, nopinone can be converted to 13 in three steps (50% yield) via a cyclobutane ring cleavage. The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl DELTA-9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

  DOI：

  10.1021/jo00024a031

文献信息

• [EN] SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DECARBOXYLATION STEP<br/>[FR] SYNTHÈSE DE PHYTOCANNABINOÏDES COMPRENANT UNE ÉTAPE DE DÉCARBOXYLATION
  申请人：UNIV SYDNEY

  公开号：WO2019033168A1

  公开（公告）日：2019-02-21

  method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound.

  将化学方程式中的羧基化植物大麻化合物（Formula I）脱羧成形成另一种植物大麻化合物（Formula II）的方法：Formula I Formula II 其中：R1选自以下组合：取代或未取代的C1-C5烷基；R2选自以下组合：OH或O；R3选自以下组合：取代或未取代的环己烯，取代或未取代的C2-C8烯烃，或取代或未取代的C2-C8二烯烃；或者R2为O，且R2和R3共同形成一个环结构，其中R2是内环原子；该方法包括在存在LiCl的情况下，加热含有羧基化植物大麻化合物和极性非质子溶剂的反应混合物，以足够时间脱羧至少部分羧化植物大麻化合物并形成植物大麻化合物。
• [EN] PROCESS FOR THE PRODUCTION OF CANNABINOIDS<br/>[FR] PROCÉDÉ DE PRODUCTION DE CANNABINOÏDES
  申请人：BERKOWITZ BARRY A

  公开号：WO2020041321A1

  公开（公告）日：2020-02-27

  A process for the preparation of substantially pure diverse known and novel cannabinoids 1 and 2, which include Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), cannabidiol (11), cannabidivarin (12) and other naturally occurring tetracyclic and tricyclic cannabinoids and other synthetic tetracyclic and tricyclic analogues, via intermediates 3, 6, 4 and 5, using a cascade sequence of allylic rearrangement, aromatization and, for the tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2, including Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8- tetrahydrocannabinol. The known and novel analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis or cannabis oil.

  一种制备基本纯净的多种已知和新型大麻素1和2的方法，其中包括Δ9-四氢大麻酚（7）、四氢大麻烯酚（9）、大麻二酚（11）、大麻二烯酚（12）以及其他天然存在的四环和三环大麻素及其他合成的四环和三环类似物，通过中间体3、6、4和5，使用烯基重排、芳香化和对于四环大麻素而言，进一步高度立体选择性和区域选择性的环化级联序列。这些合成的大麻素可以比通过已知方法分离或合成的大麻素更容易地以高纯度水平获得。其中包括Δ9-四氢大麻酚（7）、四氢大麻烯酚（9）的大麻素2，含有非常低水平的异构大麻素，例如令人不满的Δ8-四氢大麻酚。具有芳香环取代基变化的已知和新型类似物，虽然可以通过新方法轻松合成，但要从大麻或大麻油的任何成分中制备则更加困难。
• The synthesis of some 11-substituted tetrahydrocannabinol metabolites
  作者：John W. ApSimon、T. Lee Collier、Michael D. Guiver

  DOI：10.1139/v82-403

  日期：1982.11.15

  9-Bromo-11-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 3b via the epoxysulfone 4. The dehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodynamically more stable Δ⁸-aldehyde 2c, or the Δ⁹-aldehyde 1c by an intramolecularly assisted elimination. Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and 1a, respectively.

  9-溴-11-酮-大麻酚（5）是通过经过环氧磺酮4处理的酮大麻酚3b制备的。 溴醛5的脱溴反应可以控制，从而得到热力学上更稳定的Δ8-醛2c，或者通过分子内辅助消除得到Δ9-醛1c。 对不饱和醛的还原分别产生了烯丙醇代谢物2a和1a。
• 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。
• Synthesis of phytocannabinoids including a decarboxylation step
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：US10807931B2

  公开（公告）日：2020-10-20

  Method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound.

  将式 I 的羧化植物大麻素化合物脱羧以形成式 II 的植物大麻素化合物的方法： 式 I 式 II 其中：R1选自由取代或未取代的C1-C5烷基组成的组； R2选自由以下组成的组R3选自由以下物质组成的组取代或未取代的环己烯、取代或未取代的 C2-C8 烯或取代或未取代的 C2-C8 二烯；或 R2 为 O，且 R2 和 R3 一起形成环结构，其中 R2 为内环原子；其中，该方法包括在氯化锂存在下加热包含羧化植物大麻素化合物和极性壬烷溶剂的反应混合物，加热时间足以使至少一部分羧化植物大麻素化合物脱羧并形成植物大麻素化合物。