1-(2-methoxy-4-methylphenyl)-2-nitropropene | 139102-35-5

• 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: 1-(2-methoxy-4-methylphenyl)-2-nitropropene
• 英文别名: 1-(2-Methoxy-4-methylphenyl)-2-nitropropen；2-Methoxy-4-methyl-1-(2-nitroprop-1-enyl)benzene
• CAS: 139102-35-5
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: CUMQWPUFQLSAFC-UHFFFAOYSA-N

物化性质

• 沸点：
  327.0±27.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxy-4-methylphenyl)-2-nitropropene 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 46.0h， 生成 (+/-)-N-methyl-1-(2-methoxy-4-methylphenyl)-2-aminopropane
  参考文献：
  名称：

  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity

  摘要：

  Certain phenylalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors. It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors. The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other. An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = > 0.9, n = 25) between 5-HT1C and 5-HT2 affinity. None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.

  DOI：

  10.1021/jm00082a014
• 作为产物：
  描述：

  2-甲氧基-4-甲基苯甲酸甲酯 在 乙酸铵 、 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 235.5h， 生成 1-(2-methoxy-4-methylphenyl)-2-nitropropene
  参考文献：
  名称：

  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity

  摘要：

  Certain phenylalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors. It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors. The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other. An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = > 0.9, n = 25) between 5-HT1C and 5-HT2 affinity. None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.

  DOI：

  10.1021/jm00082a014

文献信息

• Structure-activity relations in psychotomimetic phenylalkylamines
  作者：F. A. B. Aldous、B. C. Barrass、K. Brewster、D. A. Buxton、D. M. Green、R. M. Pinder、P. Rich、M. Skeels、K. J. Tutt

  DOI：10.1021/jm00256a016

  日期：1974.10
• Analogs of .alpha.-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs
  作者：Beng-Thong Ho、William M. McIsaac、Rong An、L. Wayne Tansey、Kenneth E. Walker、Leo F. Englert、Michael B. Noel

  DOI：10.1021/jm00295a007

  日期：1970.1