5-(1-adamantyl)-1,3-dimethoxybenzene | 60526-86-5

• 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: 5-(1-adamantyl)-1,3-dimethoxybenzene
• 英文别名: 1-(3,5-Dimethoxyphenyl)adamantane
• CAS: 60526-86-5
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: GJINANDGVDCDMG-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188 °C
• 沸点：
  399.8±35.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-adamantyl)-1,3-dimethoxybenzene 在 18-冠醚-6 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到5-(1-adamantyl)-2-bromo-1,3-dimethoxybenzene
  参考文献：
  名称：

  Novel Adamantyl Cannabinoids as CB1 Receptor Probes

  摘要：

  In previous studies, compound 1 (AM411), a 3-(1-adamantyl) analogue of the phytocannabinoid (-)-Delta(8)-tetrahydrocannabinol (Delta(8)-THC), was shown to have improved affinity and selectivity for the CB1 receptor. In this work, we further explored the role of the 1-adamantyl group at the C-3 position in a series of tricyclic cannabinoid analogues modified at the 9-northern aliphatic hydroxyl (NAH) position. Of these, 9-hydroxymethyl hexahydrocannabinol 11 (AM4054) exhibited high CB1 affinity and full agonist profile. In the cAMP assay, the 9-hydroxymethyl cannabinol analogue 24 (AM4089) had a partial agonist profile, with high affinity and moderate selectivity for rCB1 over hCB2. In vivo results in rat models of hypothermia and analgesia were congruent with in vitro data. Our in vivo data indicate that 3-(1-adamantyl) substitution, within NAH cannabinergics, imparts improved pharmacological profiles when compared to the corresponding, traditionally used 3-dimethylheptyl analogues and identifies 11 and 24 as potentially useful in vivo CB1 cannabinergic probes.

  DOI：

  10.1021/jm4000775
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 甲烷磺酸 、 氨 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 5-(1-adamantyl)-1,3-dimethoxybenzene
  参考文献：
  名称：

  通过分散体和空气稳定的钯 (I) 二聚体实现金刚烷芳烃的选择性邻位官能化。

  摘要：

  与普遍认为不利于在严重空间位阻位点上的 Pd 催化交叉偶联相反，我们在此表明​​，由于有吸引力，C-Br 邻位金刚​​烷基的氧化加成与相应的无金刚烷基体系一样受欢迎。分散力。这使得能够开发出金刚烷基邻位 C-Br 的完全选择性芳基化和烷基化，即使受到竞争性非受阻 C-OTf 或 C-Cl 位点的挑战。该方法利用空气稳定的 PdI 二聚体，能够在 5-30 分钟内直接获得多种取代的具有治疗意义的金刚芳烃。

  DOI：

  10.1002/anie.202001326

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。
• Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate
  作者：Yukiya Sato、Kei Nakamura、Yuto Sumida、Daisuke Hashizume、Takamitsu Hosoya、Hirohisa Ohmiya

  DOI：10.1021/jacs.0c04456

  日期：2020.6.3

  The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excita-tion of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron mole-cule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond for-mations such as alkyl-aryl cross-coupling or vicinal

  叔、仲和伯烷基自由基的产生是通过硼苯基烷基硼酸酯的直接可见光激发来实现的。该系统基于有机硼分子的光物理特性。该协议适用于脱氰烷基化、Giese 加成和镍催化的碳-碳键形成，例如烯烃的烷基-芳基交叉偶联或邻位烷基芳基化，从而能够将各种 C(sp3) 片段引入到有机分子。
• Adamantyl Cannabinoids:  A Novel Class of Cannabinergic Ligands
  作者：Dai Lu、Zhaoxing Meng、Ganesh A. Thakur、Pusheng Fan、John Steed、Cindy L. Tartal、Dow P. Hurst、Patricia H. Reggio、Jeffrey R. Deschamps、Damon A. Parrish、Clifford George、Torbjörn U. C. Järbe、Richard J. Lamb、Alexandros Makriyannis

  DOI：10.1021/jm058175c

  日期：2005.7.1

  Structure-activity relationship studies have established that the aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have now synthesized a series of analogues in which a variety of adamantyl substituents were introduced at the C3 position of Delta(8)-THC. Our lead compound, (-)-3-(1-adamantyl)-Delta(8) tetrahydrocannabinol (1a, AM411), was found to have robust affinity and selectivity for the CB I receptor as well as high in vivo potency. The X-ray crystal structure of 1 a was determined. Exploration of the side chain conformational space using molecular modeling approaches has allowed us to develop cannabinoid side chain pharmacophore models for the CB1 and CB2 receptors. Our results suggest that although a bulky group at the C3 position of classical cannabinoids could be tolerated by both CB1 and CB2 binding sites, the relative orientation of that group with respect to the tricyclic component can lead to receptor subtype selectivity.
• US4087410A
  申请人：——

  公开号：US4087410A

  公开（公告）日：1978-05-02
• US4131656A
  申请人：——

  公开号：US4131656A

  公开（公告）日：1978-12-26