5-(1-heptylcyclopropyl)resorcinol | 951039-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(1-heptylcyclopropyl)resorcinol
• 英文别名: 5-(1-Heptylcyclopropyl)benzene-1,3-diol
• CAS: 951039-77-3
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: NNQNBPXJQQMZEG-UHFFFAOYSA-N

物化性质

• 沸点：
  382.4±12.0 °C(predicted)
• 密度：
  1.066±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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-heptylcyclopropyl)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-heptylcyclopropyl)-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：

  1-(3,5-dimethoxyphenyl)cyclopropanecarbonitrile 在 hexamethyldisilazide 、 二异丁基氢化铝 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 acetate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 5-(1-heptylcyclopropyl)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