1-deoxy-3-(1',1'-dimethylheptyl)-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1259509-77-7

• 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: 1-deoxy-3-(1',1'-dimethylheptyl)-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1259509-77-7
• 化学式: C₃₁H₄₉BO₃
• 分子量: 480.539
• InChiKey: JYBBLCDIBAOVGL-DNQXCXABSA-N

反应信息

• 作为反应物：
  描述：

  1-deoxy-3-(1',1'-dimethylheptyl)-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 copper(ll) bromide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以66%的产率得到JWH-383
  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：

  3-(1',1'-dimethylheptyl)-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， 反应 4.0h， 以76%的产率得到1-deoxy-3-(1',1'-dimethylheptyl)-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