1-(3,5-dimethoxyphenyl)cyclopentanecarboxaldehyde | 339094-30-3

• 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: 1-(3,5-dimethoxyphenyl)cyclopentanecarboxaldehyde
• 英文别名: (3,5-Dimethoxyphenyl)cyclopentane carboxaldehyde；1-(3,5-dimethoxyphenyl)cyclopentane-1-carbaldehyde
• CAS: 339094-30-3
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ODDXNFVRDOKBDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethoxyphenyl)cyclopentanecarboxaldehyde 在 palladium on activated charcoal 氢气 、 hexamethyldisilazide 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 78.75h， 生成 5-(1-heptylcyclopentyl)resorcinol
  参考文献：
  名称：

  C1‘-Cycloalkyl Side Chain Pharmacophore in Tetrahydrocannabinols

  摘要：

  In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1'-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1'-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1'-cyclopropyl and C1'-cyclopentyl groups are optimal pharmacophores for both receptors while the C1'-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1'-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2'-C3' cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.

  DOI：

  10.1021/jm070121a
• 作为产物：
  描述：

  3,5-二甲氧基苯基乙腈 在 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.13h， 生成 1-(3,5-dimethoxyphenyl)cyclopentanecarboxaldehyde
  参考文献：
  名称：

  大麻素侧链的药理学要求。在C1'处探测大麻素受体亚位点。

  摘要：

  我们实验室的早期工作为CB1和CB2大麻素受体结合域内存在一个亚位点提供了证据，该位点对应于经典大麻素苄基侧链位置的取代基。现在已经通过合成一系列带有C1'-环取代基的（-）-Delta（8）-四氢大麻酚类似物来探索该亚位点的存在和立体化学特征。在本文所述的化合物中，具有C1'-二硫杂环戊烷（1c），C1'-二氧戊环（2d）和环戊基（2a）取代基的化合物表现出对CB1和CB2的最高亲和力。我们使用分子建模方法更好地定义了假定亚位点的立体化学极限。体外药理测试发现1c是有效的CB1激动剂。

  DOI：

  10.1021/jm020558c

文献信息

• A New Ring-Forming Methodology for the Synthesis of Conformationally Constrained Bioactive Molecules
  作者：Demetris P. Papahatjis、Spyros Nikas、Andrew Tsotinis、Margarita Vlachou、Alexandros Makriyannis

  DOI：10.1246/cl.2001.192

  日期：2001.3

  A new, general, one pot method for introducing carbocyclic rings alpha to a nitrile moiety is described. Treatment of readily available arylacetonitriles with potassium bis(trimethylsilyl)amide and subsequent alkylation with α, ω-dibromo or dichloroalkanes in tetrahydrofuran under anhydrous conditions at 0 °C produces cycloalkyl adducts in good yields and short reaction times.

  描述了一种新的通用一锅法，用于在腈基前引入碳环。将 readily available 的芳基乙腈与氨基钾双(trimethylsilyl)处理，随后在无水条件下于0 °C的四氢呋喃中与α,ω-二溴或二氯烷烃进行烷基化，可以在短反应时间内以良好的产率生成环烷基附加物。
• Novel bicyclic and tricyclic cannabinoids
  申请人：——

  公开号：US20040236116A1

  公开（公告）日：2004-11-25

  Novel bicyclic-cannabinoids and hexahydrocannabinol analogs are presented. These compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response useful to treat a number of physiological conditions.

  本发明提供了新型双环大麻素和六氢大麻酚类似物。当以治疗有效量给个体或动物施用这些化合物时，会导致个体或动物体内该化合物的水平足够高，从而引起生理反应。这种生理反应对于治疗多种生理状况非常有用。
• Novel Bicyclic Cannabinoids
  申请人：Makriyannis Alexandros

  公开号：US20070135388A1

  公开（公告）日：2007-06-14

  Bicyclic-cannabinoids and methods of preparation and use are presented. These compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本文介绍了双环大麻素及其制备和使用方法。当以治疗有效量的这些化合物给个体或动物注射时，会在个体或动物体内产生足够高的该化合物水平，从而引起生理反应。这种生理反应可能对治疗多种生理状况有用。
• Bicyclic and tricyclic cannabinoids
  申请人：University of Connecticut

  公开号：US07285683B2

  公开（公告）日：2007-10-23

  Novel bicyclic-cannabinoids and hexahydrocannabinol analogs are presented. These compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response useful to treat a number of physiological conditions.

  本文介绍了新型的双环式大麻素和六氢大麻酚类似物。当以治疗有效剂量给个体或动物施用这些化合物时，会在个体或动物中产生足够高的该化合物水平，从而引起生理反应。这种生理反应对于治疗许多生理疾病是有用的。
• Bicyclic cannabinoids
  申请人：University of Connecticut

  公开号：US07446229B2

  公开（公告）日：2008-11-04

  Bicyclic-cannabinoids and methods of preparation and use are presented. These compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本文介绍了二环大麻素及其制备和使用方法。当以治疗有效剂量给予个体或动物时，这些化合物会在个体或动物中产生足够高的水平，从而导致生理反应。这种生理反应可能对治疗许多生理状况有用。