(+/-)-1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1,5-dimethyl-4-propylpyridine | 59381-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1,5-dimethyl-4-propylpyridine
• 英文别名: 1,3-Dimethyl-4-n-propyl-4-(3-methoxyphenyl)-1,4,5,6-tetrahydropyridine；4-(3-methoxyphenyl)-1,5-dimethyl-4-propyl-2,3-dihydropyridine
• CAS: 59381-17-8
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: CLBRVLSTLRGKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1,5-dimethyl-4-propylpyridine 生成 picenadol methyl ether
  参考文献：
  名称：

  BARNETT, CHARLES J.;COPLEY-MERRIMAN, CATHERINE R.;MAKI, JAMES, J. ORG. CHEM., 54,(1989) N0, C. 4795-4800

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二甲基-4-哌啶酮 在 仲丁基锂 作用下， 反应 2.25h， 生成 (+/-)-1,2,3,4-tetrahydro-4-(3-methoxyphenyl)-1,5-dimethyl-4-propylpyridine
  参考文献：
  名称：

  Synthesis of picenadol via metallo enamine alkylation methodology

  摘要：

  DOI：

  10.1021/jo00281a019

文献信息

• 1,3,4-Trisubstituted-4-aryl-1,4,5,6-tetra-hydropyridines
  申请人：Eli Lilly and Company

  公开号：US04175197A1

  公开（公告）日：1979-11-20

  Novel 1,3,4-trisubstituted-4-arylpiperidines are prepared by alkylating a 2,3-disubstituted-3-arylpyrroline to afford a 1,2,3-trisubstituted-3-aryl-1-pyrrolinium salt, reacting the salt with diazomethane to provide a 1,2,3-trisubstituted-3-aryl-1,2-methylene-pyrrolidinium salt, heating the pyrrolidinium salt to effect a ring expansion to the corresponding 1,3,4-trisubstituted-4-aryl-1,4,5,6-tetrahydropyridinium salt, neutralizing the salt and reducing the tetrahydropyridine to provide a 1,3,4-trisubstituted-4-arylpiperidine. The piperidines so formed are useful as pharmacological agents and as intermediates in the preparation of other piperidines of the invention. The compounds provided herein are especially useful as narcotic agonists analgesics and as narcotic antagonists.

  本发明涉及制备1,3,4-三取代-4-芳基哌啶的方法，包括烷基化2,3-二取代-3-芳基吡咯烷以得到1,2,3-三取代-3-芳基-1-吡咯铵盐，将该盐与重氮甲烷反应以提供1,2,3-三取代-3-芳基-1,2-亚甲基吡咯啉铵盐，加热吡咯啉盐以实现环扩张到相应的1,3,4-三取代-4-芳基-1,4,5,6-四氢吡啶铵盐，中和盐并还原四氢吡啶以提供1,3,4-三取代-4-芳基哌啶。所制备的哌啶化合物可用作药理学制剂和本发明的其他哌啶化合物的中间体。本发明提供的化合物特别适用于作为麻醉药物激动剂镇痛剂和麻醉药物拮抗剂。
• Analgesic method using 1,3,4-trisubstituted-4-arylpiperidines
  申请人：Eli Lilly and Company

  公开号：US04191771A1

  公开（公告）日：1980-03-04

  1,3,4-Trisubstituted-4-arylpiperidines are used to impart analgesia and to treat narcotic addiction.

  1,3,4-三取代-4-芳基哌啶被用于提供镇痛作用和治疗麻醉药物成瘾。
• 1,3,4-Trisubstituted-4-arylpiperidines and their preparation
  申请人：Eli Lilly and Company

  公开号：US04081450A1

  公开（公告）日：1978-03-28

  Novel 1,3,4-trisubstituted-4-arylpiperidines are prepared by alkylating a 2,3-disubstituted-3-arylpyrroline to afford a 1,2,3-trisubstituted-3-aryl-1-pyrrolinium salt, reacting the salt with diazomethane to provide a 1,2,3-trisubstituted-3-aryl-1,2-methylene-pyrrolidinium salt, heating the pyrrolidinium salt to effect a ring expansion to the corresponding 1,3,4-trisubstituted-4-aryl-1,4,5,6-tetrahydropyridinium salt, neutralizing the salt and reducing the tetrahydropyridine to provide a 1,3,4-trisubstituted-4-arylpiperidine. The piperidines so formed are useful as pharmacological agents and as intermediates in the preparation of other piperidines of the invention. The compounds provided herein are especially useful as narcotic agonists analgesics and as narcotic antagonists.

  通过烷基化2,3-二取代-3-芳基吡咯啉，制备了新型1,3,4-三取代-4-芳基哌啶。该方法包括：制备1,2,3-三取代-3-芳基-1-吡咯铵盐，然后与重氮甲烷反应得到1,2,3-三取代-3-芳基-1,2-亚甲基吡咯啉盐；加热吡咯啉盐以实现环扩张到相应的1,3,4-三取代-4-芳基-1,4,5,6-四氢吡啶盐；中和盐并还原四氢吡啶以提供1,3,4-三取代-4-芳基哌啶。所形成的哌啶化合物可用作药理学制剂和发明中其他哌啶化合物的中间体。本文提供的化合物特别适用于镇痛药的麻醉激动剂和麻醉拮抗剂。
• 1-Azoniabicyclo[3.1.0]hexanes
  申请人：Eli Lilly and Company

  公开号：US04115400A1

  公开（公告）日：1978-09-19

  Novel 1,3,4-trisubstituted-4-arylpiperidines are prepared by alkylating a 2,3-disubstituted-3-arylpyrroline to afford a 1,2,3-trisubstituted-3-aryl-1-pyrrolinium salt, reacting the salt with diazomethane to provide a 1,2,3-trisubstituted-3-aryl-1,2-methylene-pyrrolidinium salt, heating the pyrrolidinium salt to effect a ring expansion to the corresponding 1,3,4-trisubstituted-4-aryl-1,4,5,6-tetrahydropyridinium salt, neutralizing the salt and reducing the tetrahydropyridine to provide a 1,3,4-trisubstituted-4-arylpiperidine. The piperidines so formed are useful as pharmacological agents and as intermediates in the preparation of other piperidines of the invention. The compounds provided herein are especially useful as narcotic agonists analgesics and as narcotic antagonists.

  通过烷基化2,3-二取代-3-芳基吡咯烷制备新型1,3,4-三取代-4-芳基哌啶。该方法包括制备1,2,3-三取代-3-芳基-1-吡咯铵盐，将该盐与重氮甲烷反应得到1,2,3-三取代-3-芳基-1,2-亚甲基吡咯啉铵盐，加热吡咯啉铵盐使其环扩展至相应的1,3,4-三取代-4-芳基-1,4,5,6-四氢吡啶铵盐，中和盐并还原四氢吡啶以得到1,3,4-三取代-4-芳基哌啶。所得的哌啶化合物可用作药理学制剂和本发明其它哌啶的中间体。本文提供的化合物尤其适用于镇痛药物和镇痛拮抗剂。
• US4081450A
  申请人：——

  公开号：US4081450A

  公开（公告）日：1978-03-28