5-[1-[(1Z)-1-hexenyl]cyclopentyl]resorcinol | 941583-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-[1-[(1Z)-1-hexenyl]cyclopentyl]resorcinol
• 英文别名: 5-[1-[(Z)-hex-1-enyl]cyclopentyl]benzene-1,3-diol
• CAS: 941583-80-8
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: VMMIDNRMPRPOFS-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[1-[(1Z)-1-hexenyl]cyclopentyl]resorcinol 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (6aR-trans)-3-[1-[(1Z)-1-hexenyl]cyclopentyl]-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
  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-dimethoxy-1-[1-[(1Z)-1-hexenyl]cyclopentyl]benzene 在 B-I-9-borabicyclo[3.3.1]nonane 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以75%的产率得到5-[1-[(1Z)-1-hexenyl]cyclopentyl]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

文献信息

• 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 CANNABINOID
  申请人：The University of Connecticut

  公开号：EP1414775B1

  公开（公告）日：2012-12-19
• NOVEL BICYCLIC AND TRICYCLIC CANNABINOIDS
  申请人：The University of Connecticut

  公开号：EP1414775A2

  公开（公告）日：2004-05-06
• EP1414775A4
  申请人：——

  公开号：EP1414775A4

  公开（公告）日：2005-06-29