3,5-dimethoxy-1-[1-(5-phenoxypentyl)cyclopentyl]benzene | 1246763-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dimethoxy-1-[1-(5-phenoxypentyl)cyclopentyl]benzene
• 英文别名: 1,3-Dimethoxy-5-[1-(5-phenoxypentyl)cyclopentyl]benzene
• CAS: 1246763-39-2
• 化学式: C₂₄H₃₂O₃
• 分子量: 368.516
• InChiKey: GARQETPKDNLCFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3,5-dimethoxy-1-[1-(5-phenoxypentyl)cyclopentyl]benzene 在 四(三苯基膦)钯 、 正丁基锂 、 caesium carbonate 、 9-碘-9-硼杂二环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 15.5h， 生成 1-hydroxy-3-(1-(5-iodopentyl)cyclopentyl)-9-methoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Synthesis of Functionalized Cannabilactones

  摘要：

  使用Suzuki交叉偶联反应后跟一步脱甲基环化合成卡纳比拉克酮的新方法被提出。与我们之前的合成相比，两种关键的卡纳比拉克酮原型AM1710和AM1714以更高的总收率和更少的合成步骤被选择性地获得。这种新方法加速了在四个潜在的药效团区域进行结构修改的卡纳比拉克酮类似物的合成。

  DOI：

  10.3390/molecules25030684
• 作为产物：
  描述：

  3,5-dimethoxy-1-[1-(1,2-cis-5-phenoxypenten-1-yl)cyclopentyl]-benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3,5-dimethoxy-1-[1-(5-phenoxypentyl)cyclopentyl]benzene
  参考文献：
  名称：

  Novel 1′,1′-Chain Substituted Hexahydrocannabinols: 9β-Hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a Highly Potent Cannabinoid Receptor 1 (CB1) Agonist

  摘要：

  In pursuit of a more detailed understanding of the structural requirements for the key side chain cannabinoid pharmacophore, we have extended our SA R to cover a variety of conformationally modified side chains within the 9-keto and 9-hydroxyl tricyclic structures. OF the compounds described here. those with a seven-atom long side chain substituted with a cyclopentyl ring at Cl' position have very high affinities For both CB1 and CB2 (0.97 nM < K-1 < 5.25 nM), with no preference for either of the two receptors. However, presence of the smaller cyclobutyl group at the Cl' position leads to an optimal affinity and selectivity interaction with CB1. Thus, two of the Cl'-cyclobutyl analogues, namely. (6a R.10aR R)-3-(1-hexyl-cyclobut-1-y1)-6,6a,7,8, 10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo-[b,d]pyran-9-one and (6aR,9R, 10aR)-3-(1-hexyl-cyclobut-1-yl)-6a,7,8,9,10, 10a-hexahydro-6.6-dimethyl-6H-dibenzo[b,d]pyran-1,9 diol (7e-beta, AM2389), exhibited remarkably high affinities (0.84 and 0.16 nM respectively) and significant selectivities (16- and 26-fold, respectively) for CB1. Compound 7e-beta was found to exhibit exceptionally high in vitro and in vivo potency with a relatively long duration of action.

  DOI：

  10.1021/jm100641g

文献信息

• Synthesis of Functionalized Cannabilactones
  作者：Yingpeng Liu、Thanh C. Ho、Mohammed Baradwan、Maria Pascual Lopez-Alberca、Christos Iliopoulos-Tsoutsouvas、Spyros P. Nikas、Alexandros Makriyannis

  DOI：10.3390/molecules25030684

  日期：——

  A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compared to our earlier synthesis. The new approach expedited the synthesis of cannabilactone analogs with structural modifications at the four potential pharmacophoric regions.

  使用Suzuki交叉偶联反应后跟一步脱甲基环化合成卡纳比拉克酮的新方法被提出。与我们之前的合成相比，两种关键的卡纳比拉克酮原型AM1710和AM1714以更高的总收率和更少的合成步骤被选择性地获得。这种新方法加速了在四个潜在的药效团区域进行结构修改的卡纳比拉克酮类似物的合成。
• Novel 1′,1′-Chain Substituted Hexahydrocannabinols: 9β-Hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a Highly Potent Cannabinoid Receptor 1 (CB1) Agonist
  作者：Spyros P. Nikas、Shakiru O. Alapafuja、Ioannis Papanastasiou、Carol A. Paronis、Vidyanand G. Shukla、Demetris P. Papahatjis、Anna L. Bowman、Aneetha Halikhedkar、Xiuwen Han、Alexandros Makriyannis

  DOI：10.1021/jm100641g

  日期：2010.10.14

  In pursuit of a more detailed understanding of the structural requirements for the key side chain cannabinoid pharmacophore, we have extended our SA R to cover a variety of conformationally modified side chains within the 9-keto and 9-hydroxyl tricyclic structures. OF the compounds described here. those with a seven-atom long side chain substituted with a cyclopentyl ring at Cl' position have very high affinities For both CB1 and CB2 (0.97 nM < K-1 < 5.25 nM), with no preference for either of the two receptors. However, presence of the smaller cyclobutyl group at the Cl' position leads to an optimal affinity and selectivity interaction with CB1. Thus, two of the Cl'-cyclobutyl analogues, namely. (6a R.10aR R)-3-(1-hexyl-cyclobut-1-y1)-6,6a,7,8, 10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo-[b,d]pyran-9-one and (6aR,9R, 10aR)-3-(1-hexyl-cyclobut-1-yl)-6a,7,8,9,10, 10a-hexahydro-6.6-dimethyl-6H-dibenzo[b,d]pyran-1,9 diol (7e-beta, AM2389), exhibited remarkably high affinities (0.84 and 0.16 nM respectively) and significant selectivities (16- and 26-fold, respectively) for CB1. Compound 7e-beta was found to exhibit exceptionally high in vitro and in vivo potency with a relatively long duration of action.