2-benzyl-7-octahydro-2H-pyrido<1,2-a>pyrazine | 146367-36-4

• 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: 2-benzyl-7-octahydro-2H-pyrido<1,2-a>pyrazine
• 英文别名: 2-benzyl-7-[bis(4-fluorophenyl)methylidene]-3,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine
• CAS: 146367-36-4
• 化学式: C₂₈H₂₈F₂N₂
• 分子量: 430.541
• InChiKey: GZHIMTHRAMJWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyl-7-octahydro-2H-pyrido<1,2-a>pyrazine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 7-[bis(4-fluorophenyl)methyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine
  参考文献：
  名称：

  Synthesis and 2,7-functionalization of the bicyclic lactam 2-benzyloctahydropyrido[1,2-a]pyrazin-6-one

  摘要：

  This report describes the synthesis of the title compound 7 and its conversion into 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines, i.e., bicyclic analogues of the monocyclic piperazine drug lidoflazine. The synthesis of 7 is based on a 3-fold amino substitution of methyl 6-chlor-5-oxohexanoate (12), initiated by displacement of chlorine with N-benzyl-N'-trityl-1,2-ethanediamine. The required trielectrophile 12 was prepared readily from commercially available diethyl 2-acetyl-glutarate. The 7-position of compound 7 was functionalized through reaction of the lactam anion with benzophenone electrophiles. Further elaboration into the target compounds 8-10 involved dehydration, reduction of the lactam group, and different modes of N-debenzylation. Conformational aspects for lactam compounds 17 and 18 and the modes of ring fusion for the diastereomeric amines 9 and 10 were examined by using proton NMR and infrared spectroscopy.

  DOI：

  10.1021/jo00055a023
• 作为产物：
  描述：

  2-benzyl-7-octahydropyrido<1,2-a>pyrazin-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到2-benzyl-7-octahydro-2H-pyrido<1,2-a>pyrazine
  参考文献：
  名称：

  Synthesis and 2,7-functionalization of the bicyclic lactam 2-benzyloctahydropyrido[1,2-a]pyrazin-6-one

  摘要：

  This report describes the synthesis of the title compound 7 and its conversion into 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines, i.e., bicyclic analogues of the monocyclic piperazine drug lidoflazine. The synthesis of 7 is based on a 3-fold amino substitution of methyl 6-chlor-5-oxohexanoate (12), initiated by displacement of chlorine with N-benzyl-N'-trityl-1,2-ethanediamine. The required trielectrophile 12 was prepared readily from commercially available diethyl 2-acetyl-glutarate. The 7-position of compound 7 was functionalized through reaction of the lactam anion with benzophenone electrophiles. Further elaboration into the target compounds 8-10 involved dehydration, reduction of the lactam group, and different modes of N-debenzylation. Conformational aspects for lactam compounds 17 and 18 and the modes of ring fusion for the diastereomeric amines 9 and 10 were examined by using proton NMR and infrared spectroscopy.

  DOI：

  10.1021/jo00055a023

文献信息

• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.
• Synthesis and 2,7-functionalization of the bicyclic lactam 2-benzyloctahydropyrido[1,2-a]pyrazin-6-one
  作者：M. Ashty Saleh、Frans Compernolle、Stefan Van den Branden、Wim De Buysser、Georges Hoornaert

  DOI：10.1021/jo00055a023

  日期：1993.1

  This report describes the synthesis of the title compound 7 and its conversion into 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines, i.e., bicyclic analogues of the monocyclic piperazine drug lidoflazine. The synthesis of 7 is based on a 3-fold amino substitution of methyl 6-chlor-5-oxohexanoate (12), initiated by displacement of chlorine with N-benzyl-N'-trityl-1,2-ethanediamine. The required trielectrophile 12 was prepared readily from commercially available diethyl 2-acetyl-glutarate. The 7-position of compound 7 was functionalized through reaction of the lactam anion with benzophenone electrophiles. Further elaboration into the target compounds 8-10 involved dehydration, reduction of the lactam group, and different modes of N-debenzylation. Conformational aspects for lactam compounds 17 and 18 and the modes of ring fusion for the diastereomeric amines 9 and 10 were examined by using proton NMR and infrared spectroscopy.