1-deoxy-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1227828-17-2

• 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-Δ8-tetrahydrocannabinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-((6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-yl)-1,3,2-dioxaborolane；2-[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1227828-17-2
• 化学式: C₂₇H₄₁BO₃
• 分子量: 424.432
• InChiKey: AKWGAUCEMVTORZ-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-deoxy-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 10.0h， 以75%的产率得到JWH-460
  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：

  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

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。
• 1-Bromo-3-(1′,1′-dimethylalkyl)-1-deoxy-Δ8-tetrahydrocannabinols: New selective ligands for the cannabinoid CB2 receptor
  作者：John W. Huffman、Seon A. Hepburn、Nataliya Lyutenko、Alicia L.S. Thompson、Jenny L. Wiley、Dana E. Selley、Billy R. Martin

  DOI：10.1016/j.bmc.2010.09.061

  日期：2010.11.15

  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.