8-Azabicyclo[3.2.1]oct-2-ene,2-(3,4-dimethoxyphenyl)-8-methyl-3-(4-methylphenyl)-, (1R,5S)- | 871228-45-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 8-Azabicyclo[3.2.1]oct-2-ene,2-(3,4-dimethoxyphenyl)-8-methyl-3-(4-methylphenyl)-, (1R,5S)-
• 英文别名: 3-(4-methylphenyl)-2-(2,3-dimethoxyphenyl)-2-tropene
• CAS: 871228-45-4
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: YGMZIWDBOASLRK-AZUAARDMSA-N

物化性质

• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-Azabicyclo[3.2.1]oct-2-ene,2-(3,4-dimethoxyphenyl)-8-methyl-3-(4-methylphenyl)-, (1R,5S)- 在 palladium on activated charcoal lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 3α-(4'-methyphenyl)-2α-(3,4-dimethoxyphenyl)tropane
  参考文献：
  名称：

  Synthesis and Monoamine Transporter Binding Properties of 2,3-Diaryltropanes

  摘要：

  Synthetic procedures were developed for the synthesis of 2 beta,3 beta- and 2 alpha,3 alpha-diaryltropanes. These compounds are analogues of the 3-aryltropane-2 beta-carboxylic acid methyl ester class of monoamine uptake inhibitors, where the 2 beta-carbomethoxy group has been replaced by an aryl group. The compounds were evaluated for inhibition of radioligand binding at the dopamine, norepinephrine, and serotonin transporters (DAT, NET, and 5-HTT, respectively). The results showed that the replacement of the 2 beta-carbomethoxy group in the 3-aryltropane class with a 2 beta-aryl group led to compounds possessing very similar monoamine transporter binding properties. However, the 2 beta,3 beta-diaryltropanes tended to be more potent at the DAT and more selective for the DAT relative to the NET and 5-HTT. One of the most interesting compounds was 3 beta-(4-methylphenyl)-2 beta-(4-methylphenyl)tropane (3d), which showed an IC50 of 1.23 nM at the DAT with 289- and 185-fold selectivity for the DAT relative to the NET and 5-HTT. The 2 alpha,3 alpha-diaryltropanes were much less potent at all three transporters than 2 beta,3 beta-diaryltropanes.

  DOI：

  10.1021/jm0582423
• 作为产物：
  描述：

  (R)-2-carbomethoxy-3-(4-methylphenyl)-2-tropene 在 盐酸 、 氢氧化钾 、 四(三苯基膦)钯 、 二苯基膦叠氮化物 、 sodium hydride 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.5h， 生成 8-Azabicyclo[3.2.1]oct-2-ene,2-(3,4-dimethoxyphenyl)-8-methyl-3-(4-methylphenyl)-, (1R,5S)-
  参考文献：
  名称：

  Synthesis and Monoamine Transporter Binding Properties of 2,3-Diaryltropanes

  摘要：

  Synthetic procedures were developed for the synthesis of 2 beta,3 beta- and 2 alpha,3 alpha-diaryltropanes. These compounds are analogues of the 3-aryltropane-2 beta-carboxylic acid methyl ester class of monoamine uptake inhibitors, where the 2 beta-carbomethoxy group has been replaced by an aryl group. The compounds were evaluated for inhibition of radioligand binding at the dopamine, norepinephrine, and serotonin transporters (DAT, NET, and 5-HTT, respectively). The results showed that the replacement of the 2 beta-carbomethoxy group in the 3-aryltropane class with a 2 beta-aryl group led to compounds possessing very similar monoamine transporter binding properties. However, the 2 beta,3 beta-diaryltropanes tended to be more potent at the DAT and more selective for the DAT relative to the NET and 5-HTT. One of the most interesting compounds was 3 beta-(4-methylphenyl)-2 beta-(4-methylphenyl)tropane (3d), which showed an IC50 of 1.23 nM at the DAT with 289- and 185-fold selectivity for the DAT relative to the NET and 5-HTT. The 2 alpha,3 alpha-diaryltropanes were much less potent at all three transporters than 2 beta,3 beta-diaryltropanes.

  DOI：

  10.1021/jm0582423