benzyl 3-allyl-4-oxo-piperidine-1-carboxylate | 140211-12-7

• 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: benzyl 3-allyl-4-oxo-piperidine-1-carboxylate
• 英文别名: benzyl 3-allyl-4-oxopiperidine-1-carboxylate；Benzyl 3-allyl-4-oxo-piperidine-1-carboxylate；benzyl 4-oxo-3-prop-2-enylpiperidine-1-carboxylate
• CAS: 140211-12-7
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: LZCNMAFIMZDETK-UHFFFAOYSA-N

物化性质

• 沸点：
  406.8±45.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 3-allyl-4-oxo-piperidine-1-carboxylate 在 偶氮二异丁腈 、 三氟化硼乙醚 、 potassium tert-butylate 、 triethyloxonium fluoroborate 作用下， 以 苯 为溶剂， 反应 20.58h， 生成 benzyl (trans)-5-oxooctahydro-2H-cyclopenta[c]pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acids

  摘要：

  A series of novel 7-[amino-substituted azabicycloalkanyl]-6-fluoro-1-substituted quinolinecarboxylic acids (18-53) have been prepared and their antibacterial activities evaluated. These compounds are characterized structurally by a new amino-substituted azabicyclo[3.3.0]octane,-[4.3.0]nonane and -[5.3.0]decane ring systems at the 7-position of quinolonecarboxylic acids. To compare the biological activities of enantiomers, (+)-7[(1S, 5R)- and (-)-7[(1R, 5S)-1-aminomethyl-3-azabicyclo[3.3.0]-octan-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylic acid hydrochloride (43, 44) were synthesized and evaluated for antibacterial activity. Compound 43 was more potent than 44 against both Gram-positive and Gram-negative organisms. The structure-activity relationships of these quinolonecarboxylic acids are also discussed.

  DOI：

  10.1016/0223-5234(91)90131-6
• 作为产物：
  描述：

  benzyl 4-vinyl-3,6-dihydropyridine-1(2H)-carboxylate 在 对甲苯磺酸 、 烯丙醇 作用下， 生成 benzyl 3-allyl-4-oxo-piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acids

  摘要：

  A series of novel 7-[amino-substituted azabicycloalkanyl]-6-fluoro-1-substituted quinolinecarboxylic acids (18-53) have been prepared and their antibacterial activities evaluated. These compounds are characterized structurally by a new amino-substituted azabicyclo[3.3.0]octane,-[4.3.0]nonane and -[5.3.0]decane ring systems at the 7-position of quinolonecarboxylic acids. To compare the biological activities of enantiomers, (+)-7[(1S, 5R)- and (-)-7[(1R, 5S)-1-aminomethyl-3-azabicyclo[3.3.0]-octan-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylic acid hydrochloride (43, 44) were synthesized and evaluated for antibacterial activity. Compound 43 was more potent than 44 against both Gram-positive and Gram-negative organisms. The structure-activity relationships of these quinolonecarboxylic acids are also discussed.

  DOI：

  10.1016/0223-5234(91)90131-6

文献信息

• Fused Piperidine Amides as Modulators of Ion Channels
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160159815A1

  公开（公告）日：2016-06-09

  The invention relates to fused piperidine amides useful as inhibitors of ion channels for the treatment of pain. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及融合哌啶酰胺，其作为离子通道的抑制剂用于治疗疼痛。本发明还提供了包括本发明化合物的药学上可接受的组合物以及使用这些组合物治疗各种疾病的方法。
• Fused piperidine amides as modulators of ion channels
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US10233191B2

  公开（公告）日：2019-03-19

  The invention relates to fused piperidine amides useful as inhibitors of ion channels for the treatment of pain. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及可用作治疗疼痛的离子通道抑制剂的融合哌啶酰胺。本发明还提供了包含本发明化合物的药学上可接受的组合物，以及使用该组合物治疗各种疾病的方法。
• [EN] FUSED PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS<br/>[FR] AMIDES DE PIPÉRIDINE FUSIONNÉS UTILES EN TANT QUE MODULATEURS DE CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2015006280A9

  公开（公告）日：2015-05-14
• Synthesis of Fused Bicyclic Piperidines: Potential Bioactive Templates for Medicinal Chemistry
  作者：Jinglan Zhou、Erica L. Campbell-Conroy、Alina Silina、Johnny Uy、Fabrice Pierre、Dennis J. Hurley、Nicole Hilgraf、Bryan A. Frieman、Michael P. DeNinno

  DOI：10.1021/jo501967m

  日期：2015.1.2

  An array of six pyridyl-substituted fused bicyclic piperidines was prepared as novel cores for medicinal chemistry. For maximum diversity, the size of the fused ring varied from three to six atoms and contained up to two oxygen atoms. The pyridine ring was incorporated to improve physicochemical properties and to challenge the robustness of the chemistry. The presence of the pyridine did interfere with our initial approaches to these molecules, and in several instances, a blocking strategy had to be employed. These new scaffolds possess high sp3 character and may prove useful in multiple medicinal chemistry applications.
• FUSED PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS
  申请人：Vertex Pharmaceuticals Inc.

  公开号：EP3019478A1

  公开（公告）日：2016-05-18