trans-2-benzyl-7-(diphenylhydroxymethyl)octahydropyrido<1,2-a>pyrazin-6-one

• 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: trans-2-benzyl-7-(diphenylhydroxymethyl)octahydropyrido<1,2-a>pyrazin-6-one
• 英文别名: trans-2-benzyl-7-(diphenylhydroxymethyl)octahydropyrido[1,2-a]pyrazin-6-one；(7S,9aS)-2-benzyl-7-[hydroxy(diphenyl)methyl]-3,4,7,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazin-6-one
• 化学式: C₂₈H₃₀N₂O₂
• 分子量: 426.558
• InChiKey: VJGKWDKEFGUYFY-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-benzyl-7-(diphenylhydroxymethyl)octahydropyrido<1,2-a>pyrazin-6-one 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-benzyl-7-(diphenylmethylene)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
• 作为产物：
  描述：

  diethyl 2-(bromoacetyl)glutarate 在 盐酸 、 sodium cyanoborohydride 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 7.08h， 生成 trans-2-benzyl-7-(diphenylhydroxymethyl)octahydropyrido<1,2-a>pyrazin-6-one
  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

• 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.