(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol | 1972-08-3

• 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: (6aR,10aS)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• 英文别名: 6H-Dibenzo(b,d)pyran-1-ol, 6a-beta,7,8,10-a-beta-tetrahydro-3-pentyl-6,6,9-trimethyl-, (+-)-Z-；(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 1972-08-3
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: CYQFCXCEBYINGO-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 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

• 作为产物：
  描述：

  cannabidiol 在 三异丁基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以432 mg的产率得到(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  [EN] CATALYTIC CANNABINOID PROCESSES AND PRECURSORS
  [FR] PROCÉDÉS ET PRÉCURSEURS DE CANNABINOÏDES CATALYTIQUES

  摘要：

  本公开涉及新的大麻素磺酸酯和它们的制备大麻素的过程。该公开还涉及使用催化剂和催化过程从大麻素磺酸酯制备大麻素。

  公开号：

  WO2020232545A1

文献信息

• Stereodivergent Total Synthesis of Δ⁹-Tetrahydrocannabinols
  作者：Michael A. Schafroth、Giuseppe Zuccarello、Simon Krautwald、David Sarlah、Erick M. Carreira

  DOI：10.1002/anie.201408380

  日期：2014.12.8

  All four stereoisomers of Δ9‐tetrahydrocannabinol (Δ9‐THC) were synthesized in concise fashion using stereodivergent dual catalysis. Thus, following identical synthetic sequences and applying identical reaction conditions to the same set of starting materials, selective access to the four stereoisomers of THC was achieved in five steps.

  的所有四种立体异构体Δ 9 -四氢大麻酚（Δ 9 -THC）是在简洁的方式使用双stereodivergent催化合成。因此，遵循相同的合成顺序，并将相同的反应条件应用于相同的起始原料组，可以通过五个步骤选择性地获得THC的四种立体异构体。
• [EN] (+)-CIS TETRAHYDROCANNABINOL ((+)-CIS-THC) FOR USE AS A MEDICAMENT<br/>[FR] (+)-CIS TÉTRAHYDROCANNABINOL ( (+)-CIS-THC) POUR UNE UTILISATION EN TANT QUE MÉDICAMENT
  申请人：GW RES LTD

  公开号：WO2021079136A1

  公开（公告）日：2021-04-29

  The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (+)-cis tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (+)-cis-THC has been found to occur in low concentrations in particular cannabis plant strains which have been bred to produce cannabidiol (CBD) as the dominant cannabinoid. Furthermore, the cannabinoid can be produced by synthetic means.

  本发明涉及一种四氢大麻酚（THC）型大麻素化合物，用作药物。THC型大麻素是(-)-反式四氢大麻酚的对映体，它是一种天然存在的大麻素，可在经过育种以产生THC为主要大麻素的大麻植物品种中找到。特定的对映体(+)-顺式四氢大麻酚已被发现具有与天然存在的(-)-反式THC不同的特性。大麻素(+)-顺式THC已被发现以低浓度存在于特定的大麻植物品种中，这些品种经过育种以产生大麻二酚（CBD）作为主要大麻素。此外，这种大麻素可以通过合成方式生产。
• [EN] (-)-CIS TETRAHYDROCANNABINOL ((-)-CIS-THC) FOR USE AS A MEDICAMENT<br/>[FR] (-)-CIS-TÉTRAHYDROCANNABINOL ((-)-CIS-THC) DESTINÉ À ÊTRE UTILISÉ EN TANT QUE MÉDICAMENT
  申请人：GW RES LTD

  公开号：WO2021079135A1

  公开（公告）日：2021-04-29

  The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (-)-cis tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (-)-cis-THC has been found to occur in low concentrations in particular cannabis plant strains which have been bred to produce cannabidiol (CBD) as the dominant cannabinoid. Furthermore, the cannabinoid can be produced by synthetic means.

  本发明涉及一种用作药物的四氢大麻酚（THC）类大麻素化合物。这种THC类大麻素是(-)-反式四氢大麻酚的对映体，后者是一种天然存在的大麻素，在已经培育出THC作为主要大麻素的大麻植物品系中可以找到。特定的对映体(-)-顺式四氢大麻酚已发现具有与天然存在的(-)-反式THC不同的性质。(-)-顺式THC已发现以低浓度存在于特定的大麻植物品系中，这些植物品系已经被培育出以大麻二酚（CBD）作为主要大麻素。此外，这种大麻素可以通过合成手段生产。
• CATALYTIC CANNABINOID PROCESSES AND PRECURSORS
  申请人：KARE CHEMICAL TECHNOLOGIES INC.

  公开号：US20220220089A1

  公开（公告）日：2022-07-14

  The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.
• (+)-CIS TETRAHYDROCANNABINOL ((+)-CIS-THC) FOR USE AS A MEDICAMENT
  申请人：GW Research Limited

  公开号：US20220387377A1

  公开（公告）日：2022-12-08

  The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (−)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (+)-cis tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (−)-trans-THC. The cannabinoid (+)-cis-THC has been found to occur in low concentrations in particular cannabis plant strains which have been bred to produce cannabidiol (CBD) as the dominant cannabinoid. Furthermore, the cannabinoid can be produced by synthetic means.