Δ8-tetrahydrocannabinyl trifluoromethanesulfonate | 1227828-16-1

• 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: Δ8-tetrahydrocannabinyl trifluoromethanesulfonate
• 英文别名: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-yl trifluoromethanesulfonate；[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-yl] trifluoromethanesulfonate
• CAS: 1227828-16-1
• 化学式: C₂₂H₂₉F₃O₄S
• 分子量: 446.531
• InChiKey: MHFUHVLMJZQNLR-IAGOWNOFSA-N

物化性质

• 沸点：
  458.1±45.0 °C(predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Δ8-tetrahydrocannabinyl trifluoromethanesulfonate 、 频那醇硼烷 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三乙胺 作用下， 以 乙腈 为溶剂， 以65%的产率得到1-deoxy-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  1-Bromo-3-(1′,1′-dimethylalkyl)-1-deoxy-Δ8-tetrahydrocannabinols: New selective ligands for the cannabinoid CB2 receptor

  摘要：

  Delta(8)-Tetrahydrocannabinol (26), 3-(1',1'-dimethylbutyl)- (12), 3-(1',1'-dimethylpentyl)- (13), 3-(1',1'-dimethylhexyl)- (14) and 3-(1',1'-dimethylheptyl)-Delta(8)-tetrahydrocannabinol (15) have been converted into the corresponding 1-bromo-1-deoxy-Delta(8)-tetrahydrocannabinols (25, 8-11). This was accomplished using a protocol developed in our laboratory in which the trifluoromethanesulfonate of a phenol undergoes palladium mediated coupling with pinacolborane. Reaction of this dioxaborolane with aqueous-methanolic copper(II) bromide provides the aryl bromide. The affinities of these bromo cannabinoids for the cannabinoid CB1 and CB2 receptors were determined. All of these compounds showed selectivity for the CB2 receptor and one of them, 1-bromo-1-deoxy-3-(1',1'-dimethylhexyl)-Delta(8)-tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28 nM) affinity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.061
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (-)-Δ8-四氢大麻酚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到Δ8-tetrahydrocannabinyl trifluoromethanesulfonate
  参考文献：
  名称：

  1-Bromo-3-(1′,1′-dimethylalkyl)-1-deoxy-Δ8-tetrahydrocannabinols: New selective ligands for the cannabinoid CB2 receptor

  摘要：

  Delta(8)-Tetrahydrocannabinol (26), 3-(1',1'-dimethylbutyl)- (12), 3-(1',1'-dimethylpentyl)- (13), 3-(1',1'-dimethylhexyl)- (14) and 3-(1',1'-dimethylheptyl)-Delta(8)-tetrahydrocannabinol (15) have been converted into the corresponding 1-bromo-1-deoxy-Delta(8)-tetrahydrocannabinols (25, 8-11). This was accomplished using a protocol developed in our laboratory in which the trifluoromethanesulfonate of a phenol undergoes palladium mediated coupling with pinacolborane. Reaction of this dioxaborolane with aqueous-methanolic copper(II) bromide provides the aryl bromide. The affinities of these bromo cannabinoids for the cannabinoid CB1 and CB2 receptors were determined. All of these compounds showed selectivity for the CB2 receptor and one of them, 1-bromo-1-deoxy-3-(1',1'-dimethylhexyl)-Delta(8)-tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28 nM) affinity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.061

文献信息

• FLUORINATION OF ORGANIC COMPOUNDS
  申请人：Ritter Tobias

  公开号：US20110312903A1

  公开（公告）日：2011-12-22

  Methods for fluorinating organic compounds are described herein.

  本文描述了有机化合物氟化的方法。
• Fluorination of organic compounds
  申请人：Ritter Tobias

  公开号：US09024093B2

  公开（公告）日：2015-05-05

  Methods for fluorinating organic compounds are described herein.

  本文描述了有机化合物氟化的方法。
• Iron-Catalyzed Hydrobenzylation: Stereoselective Synthesis of (−)-Eugenial C
  作者：Xu-cheng Gan、Simona Kotesova、Alberto Castanedo、Samantha A. Green、Søren Lau Borcher Møller、Ryan A. Shenvi

  DOI：10.1021/jacs.3c05428

  日期：2023.7.26

  catalysis to merge the two cycles. Here, we report an iron-only cross-coupling via putative MHAT/SH2 steps that solves a key stereochemical problem in the synthesis of meroterpenoid eugenial C and obviates the need for nickel. The concise synthesis benefits from a conformationally locked o,o′-disubstituted benzyl bromide and a locally sourced chiral pool terpene coupling partner.

  金属氢化物氢原子转移（MHAT）已成为通过氢官能化从烯烃形成季碳的有用工具。迄今为止，烯烃与 sp 3伴侣的交叉偶联方法依赖于异双金属催化来合并两个循环。在这里，我们通过假定的 MHAT/S H 2 步骤报告了仅铁的交叉偶联，该步骤解决了类萜 eugenial C 合成中的关键立体化学问题，并且消除了对镍的需要。简洁的合成得益于构象锁定的o,o'-二取代苄基溴和本地来源的手性池萜烯偶联伴侣。
• US9024093B2
  申请人：——

  公开号：US9024093B2

  公开（公告）日：2015-05-05
• [EN] FLUORINATION OF ORGANIC COMPOUNDS<br/>[FR] FLUORATION DE COMPOSÉS ORGANIQUES
  申请人：HARVARD COLLEGE

  公开号：WO2010059943A2

  公开（公告）日：2010-05-27

  Methods for fluorinating organic compounds are described herein.