[(6aR,9R,10aR)-1,9-bis(methoxymethoxy)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate | 1236197-56-0

• 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-bis(methoxymethoxy)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate
• CAS: 1236197-56-0
• 化学式: C₂₀H₂₇F₃O₈S
• 分子量: 484.491
• InChiKey: DSUWRMMHYAZEHM-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(6aR,9R,10aR)-1,9-bis(methoxymethoxy)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl] trifluoromethanesulfonate 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium hexamethyldisilazane 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 17.5h， 生成 1-((6aR,9R,10aR)-1,9-bis(methoxymethoxy)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-3-yl)heptan-1-one
  参考文献：
  名称：

  C 1'-氮杂环烷基六氢大麻酚

  摘要：

  我们报告了新型的大麻素配体，即C 1'-氮杂环烷基六氢大麻酚的设计，合成和生物学评估。我们的合成方法利用了先进的通用手性中间体三氟甲磺酸酯，所有类似物都可以从中衍生得到。关键的合成步骤涉及微波辅助的Liebeskind–Srogl C–C交叉偶联和钯催化的脱羧偶联反应。发现C 1'- N-甲基氮杂环丁烷基和C 1'- N-甲基吡咯烷基类似物是CB1和CB2大麻素受体的高亲和力配体。

  DOI：

  10.1021/acs.joc.7b00988
• 作为产物：
  描述：

  (6aR,10aR)-1,3-dihydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-benzo[c]chromen-9-one 在 sodium tetrahydroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 [(6aR,9R,10aR)-1,9-bis(methoxymethoxy)-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

文献信息

• C3-Heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor
  作者：Darryl D. Dixon、Marcus A. Tius、Ganesh A. Thakur、Han Zhou、Anna L. Bowman、Vidyanand G. Shukla、Yan Peng、Alexandros Makriyannis

  DOI：10.1016/j.bmcl.2012.06.013

  日期：2012.8

  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.
• <i>C</i>1′-Azacycloalkyl Hexahydrocannabinols
  作者：Thanh C. Ho、Naoyuki Shimada、Marcus A. Tius、Spyros P. Nikas、Wen Zhang、Alexandros Makriyannis

  DOI：10.1021/acs.joc.7b00988

  日期：2017.8.4

  We report the design, synthesis, and biological evaluation of a novel class of cannabinergic ligands, namely C1′-azacycloalkyl hexahydrocannabinols. Our synthetic approaches utilize an advanced common chiral intermediate triflate from which all analogues could be derived. Key synthetic steps involve microwave-assisted Liebeskind–Srogl C–C cross-coupling and palladium-catalyzed decarboxylative coupling

  我们报告了新型的大麻素配体，即C 1'-氮杂环烷基六氢大麻酚的设计，合成和生物学评估。我们的合成方法利用了先进的通用手性中间体三氟甲磺酸酯，所有类似物都可以从中衍生得到。关键的合成步骤涉及微波辅助的Liebeskind–Srogl C–C交叉偶联和钯催化的脱羧偶联反应。发现C 1'- N-甲基氮杂环丁烷基和C 1'- N-甲基吡咯烷基类似物是CB1和CB2大麻素受体的高亲和力配体。