[(6aR,9R,10aR)-1,9-dihydroxy-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate | 1236197-54-8

• 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,9R,10aR)-1,9-dihydroxy-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate
• CAS: 1236197-54-8
• 化学式: C₁₆H₁₉F₃O₆S
• 分子量: 396.384
• InChiKey: WQXAMXHRUWRPSI-FBIMIBRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(6aR,9R,10aR)-1,9-dihydroxy-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 2,6-二叔丁基-4-甲基苯酚 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 [(6aR,9R,10aR)-1,9-bis(methoxymethoxy)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-(1,3-thiazol-4-yl)methanone
  参考文献：
  名称：

  C3-Heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor

  摘要：

  A series of tricyclic cannabinoids incorporating a heteroaroyl group at C3 were prepared as probes to explore the binding site(s) of the CB1 and CB2 receptors. This relatively unexplored structural motif is shown to be CB2 selective with K-i values at low nanomolar concentrations when the heteroaromatic group is 3-benzothiophenyl (41) or 3-indolyl (50). When photoactivated, the lead compound 41 was shown to successfully label the CB2 receptor through covalent attachment at the active site while 50 failed to label. The benzothiophenone moiety may be a photoactivatable moiety suitable for selective labeling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.013
• 作为产物：
  描述：

  [(6aR,10aR)-1-hydroxy-6,6-dimethyl-9-oxo-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-3-yl] trifluoromethanesulfonate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到[(6aR,9R,10aR)-1,9-dihydroxy-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  C3-Heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor

  摘要：

  A series of tricyclic cannabinoids incorporating a heteroaroyl group at C3 were prepared as probes to explore the binding site(s) of the CB1 and CB2 receptors. This relatively unexplored structural motif is shown to be CB2 selective with K-i values at low nanomolar concentrations when the heteroaromatic group is 3-benzothiophenyl (41) or 3-indolyl (50). When photoactivated, the lead compound 41 was shown to successfully label the CB2 receptor through covalent attachment at the active site while 50 failed to label. The benzothiophenone moiety may be a photoactivatable moiety suitable for selective labeling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.013