1,3-dimethoxy-5-(3-phenylpropyl)benzene | 289889-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-dimethoxy-5-(3-phenylpropyl)benzene
• 英文别名: 1-(3,5-dimethoxyphenyl)-3-phenylpropane
• CAS: 289889-83-4
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: GTUABZUGULOCSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-5-(3-phenylpropyl)benzene 在 正丁基锂 、 ammonium acetate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 1-[2,6-dimethoxy-4-(3-phenylpropyl)phenyl]-2-nitropropene
  参考文献：
  名称：

  1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT_2A Partial Agonists

  摘要：

  Phenylalkylamines such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; Pa) and its corresponding iodo derivative DOI (2) are commonly used 5-HT2 serotonin agonists. Previous studies have established that the 2,5-dimethoxy substitution pattern found in these compounds is optimal for high affinity at 5-HT2A receptors and that substituents at the 4-position can modulate affinity over a wide range. We have previously shown, however, that when the 4-position is substituted with a 3-phenylpropyl substituent (i.e., 3), the compound binds with an affinity comparable to that of Pa but that it possesses 5-HT2A antagonist character. The present study examined the structure-affinity relationships of 3, and the results were very much unexpected. That is, the 2,5-dimethoxy substitution pattern of 3 is not required for high affinity. Either of the two methoxy groups can be removed without untoward effect on affinity, and relocation of the methoxy substituents actually enhances affinity by as much as an order of magnitude. None of the compounds displayed more than 20-fold selectivity for 5-HT2A over 5-HT2C receptors. In addition, several were demonstrated to act as 5-HT2A partial agonists. As such, the results of this study suggest that the structure-affinity relationships of phenylalkylamines as 5-HT2A ligands now be reinvestigated in greater detail.

  DOI：

  10.1021/jm9906062
• 作为产物：
  描述：

  乙基溴苯 在 三甲基氯硅烷 、 碘 、 magnesium 、 乙腈 、 sodium iodide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 26.0h， 生成 1,3-dimethoxy-5-(3-phenylpropyl)benzene
  参考文献：
  名称：

  1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT_2A Partial Agonists

  摘要：

  Phenylalkylamines such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; Pa) and its corresponding iodo derivative DOI (2) are commonly used 5-HT2 serotonin agonists. Previous studies have established that the 2,5-dimethoxy substitution pattern found in these compounds is optimal for high affinity at 5-HT2A receptors and that substituents at the 4-position can modulate affinity over a wide range. We have previously shown, however, that when the 4-position is substituted with a 3-phenylpropyl substituent (i.e., 3), the compound binds with an affinity comparable to that of Pa but that it possesses 5-HT2A antagonist character. The present study examined the structure-affinity relationships of 3, and the results were very much unexpected. That is, the 2,5-dimethoxy substitution pattern of 3 is not required for high affinity. Either of the two methoxy groups can be removed without untoward effect on affinity, and relocation of the methoxy substituents actually enhances affinity by as much as an order of magnitude. None of the compounds displayed more than 20-fold selectivity for 5-HT2A over 5-HT2C receptors. In addition, several were demonstrated to act as 5-HT2A partial agonists. As such, the results of this study suggest that the structure-affinity relationships of phenylalkylamines as 5-HT2A ligands now be reinvestigated in greater detail.

  DOI：

  10.1021/jm9906062

文献信息

• <i>B</i>-Alkyl sp³–sp² Suzuki–Miyaura Couplings under Mild Aqueous Micellar Conditions
  作者：Nicholas R. Lee、Roscoe T. H. Linstadt、Danielle J. Gloisten、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1021/acs.orglett.8b00961

  日期：2018.5.18

  B-sp3-alkyl reagents for Suzuki–Miyaura couplings under aqueous micellar catalysis conditions is reported. Studies as to substrate scope, use in a four-step one-pot sequence, and reaction medium recycling exemplify the synthetic utility of this technology. OBBD (B-alkyl-9-oxa-10-borabicyclo[3.3.2]decane) derivatives are easily made and utilized for couplings under mild conditions. Comparisons were also

  据报道，在水胶束催化条件下，将B -sp 3-烷基试剂用于Suzuki-Miyaura偶联。关于底物范围的研究，在四步一锅法中的使用以及反应介质的循环利用，例证了该技术的合成效用。OBBD（B-烷基-9-氧杂-10-borabicyclo [3.3.2]癸烷）衍生物很容易制备，并用于温和条件下的偶联。还比较了OBBD和作为反应伙伴的9-BBN（B-烷基-9-硼环[3.3.1]壬烷）衍生物。