3-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]benzonitrile | 1046146-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]benzonitrile
• CAS: 1046146-17-1
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: XGTZWYUSOQUHSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]benzonitrile 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以97.2%的产率得到3-[1-(3,5-dihydroxy-phenyl)-1-methyl-ethyl]-benzonitrile
  参考文献：
  名称：

  Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

  摘要：

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.034
• 作为产物：
  描述：

  1-[1-(3-溴-苯基)-1-甲基-乙基]-3,5-二甲氧基-苯 、 氰化亚铜 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]benzonitrile
  参考文献：
  名称：

  Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

  摘要：

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.034