5-(m-methoxyphenyl)-9-ethylidene-2-methylmorphan | 107383-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-(m-methoxyphenyl)-9-ethylidene-2-methylmorphan
• CAS: 107383-40-4
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: CNXJKLOFFTZBMX-ROUUACIJSA-N

物化性质

• 沸点：
  378.2±42.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  5-(m-methoxyphenyl)-9-ethylidene-2-methylmorphan 在 氢溴酸 作用下， 反应 13.0h， 以38%的产率得到4a-ethyl-2,4,a,5,6,7,7a-hexahydro-4-(3-hydroxyphenyl)-1-methyl-1H-1-pyrindine
  参考文献：
  名称：

  Hexahydro-1H-1-pyrindines from acid rearrangement of 9-alkylidene-5-(m-methoxyphenyl)-2-methylmorphans. Structural type of narcotic antagonists

  摘要：

  9-Methylene- and 9-ethylidene-5-(m-methoxyphenyl)-2-methylmorphans (1, 2) and refluxing 48% HBr have given rearrangement products 3 and 4, respectively. The structure of 4 [4a-ethyl-2,4a,5,6,7,7a-hexahydro-4-(3-hydroxyphenyl)-1-methyl-1H-1- pyrindine] was determined by X-ray crystallography and that of 3 [1,4a-dimethyl-2,4a,5,6,7,7a-hexahydro-4-(3-hydroxyphenyl)-1-methyl-1H- pyrindine] follows from analogy and NMR data. Compounds 3 and 4 are opioid antagonists of about the potency of nalorphine in the tail-flick vs. morphine assay and precipitate a complete abstinence syndrome in morphine-dependent monkeys. Both are nearly devoid of antinociceptive activity and they have about 0.025 times the affinity of nalorphine for the mu opioid receptor.

  DOI：

  10.1021/jm00388a037
• 作为产物：
  描述：

  乙基三苯基溴化膦 、 5-(m-methoxyphenyl)-2-methyl-9-oxomorphan 在 sodium hydride 作用下， 生成 5-(m-methoxyphenyl)-9-ethylidene-2-methylmorphan
  参考文献：
  名称：

  Hexahydro-1H-1-pyrindines from acid rearrangement of 9-alkylidene-5-(m-methoxyphenyl)-2-methylmorphans. Structural type of narcotic antagonists

  摘要：

  9-Methylene- and 9-ethylidene-5-(m-methoxyphenyl)-2-methylmorphans (1, 2) and refluxing 48% HBr have given rearrangement products 3 and 4, respectively. The structure of 4 [4a-ethyl-2,4a,5,6,7,7a-hexahydro-4-(3-hydroxyphenyl)-1-methyl-1H-1- pyrindine] was determined by X-ray crystallography and that of 3 [1,4a-dimethyl-2,4a,5,6,7,7a-hexahydro-4-(3-hydroxyphenyl)-1-methyl-1H- pyrindine] follows from analogy and NMR data. Compounds 3 and 4 are opioid antagonists of about the potency of nalorphine in the tail-flick vs. morphine assay and precipitate a complete abstinence syndrome in morphine-dependent monkeys. Both are nearly devoid of antinociceptive activity and they have about 0.025 times the affinity of nalorphine for the mu opioid receptor.

  DOI：

  10.1021/jm00388a037