4-(2,5-dimethoxyphenyl)-4-phenethyl-1-methyl-1,2,3,4-tetrahydropyridine | 1161415-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,5-dimethoxyphenyl)-4-phenethyl-1-methyl-1,2,3,4-tetrahydropyridine
• 英文别名: 4-(2,5-Dimethoxyphenyl)-1-methyl-4-(2-phenylethyl)-2,3-dihydropyridine
• CAS: 1161415-82-2
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: PNPJGXUTRZIIGT-UHFFFAOYSA-N

物化性质

• 沸点：
  490.2±45.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,5-dimethoxyphenyl)-4-phenethyl-1-methyl-1,2,3,4-tetrahydropyridine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Probes for Narcotic Receptor Mediated Phenomena. 38. An Expeditious Synthesis of rac-cis-4a-Ethyl-2-methyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol and rac-cis-2-Methyl-4a-phenethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol

  摘要：

  A high-yielding five-step synthesis of cis-benzofuropyridin-6-ols provided an improved route to compounds with low to subnanomolar affinity at opioid receptors and high antinociceptive potency. This synthesis provided the known rac-cis-4a-etbyl-2-methyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3c]pyridin-6-ol (1a) in high yield, and the novel rac-cis-2-methyl-4a-phenethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol (1b). It was achieved using NBS to prepare the key intermediate 7. Di-demethylation followed by subsequent displacement of the bromine by the phenolic ion in hot Et3N gave the desired 1a. The structure of la was confirmed by X-ray crystallography.

  DOI：

  10.3987/com-09-s(d)84
• 作为产物：
  描述：

  4-(2,5-dimethoxyphenyl)-1-methyl-1,2,3,6-tetrahydropyridine 、 乙基溴苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以59%的产率得到4-(2,5-dimethoxyphenyl)-4-phenethyl-1-methyl-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Probes for Narcotic Receptor Mediated Phenomena. 38. An Expeditious Synthesis of rac-cis-4a-Ethyl-2-methyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol and rac-cis-2-Methyl-4a-phenethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol

  摘要：

  A high-yielding five-step synthesis of cis-benzofuropyridin-6-ols provided an improved route to compounds with low to subnanomolar affinity at opioid receptors and high antinociceptive potency. This synthesis provided the known rac-cis-4a-etbyl-2-methyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3c]pyridin-6-ol (1a) in high yield, and the novel rac-cis-2-methyl-4a-phenethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol (1b). It was achieved using NBS to prepare the key intermediate 7. Di-demethylation followed by subsequent displacement of the bromine by the phenolic ion in hot Et3N gave the desired 1a. The structure of la was confirmed by X-ray crystallography.

  DOI：

  10.3987/com-09-s(d)84