2,5-二氮杂双环[2.2.2]辛烷-3,6-二酮 | 1004-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,5-二氮杂双环[2.2.2]辛烷-3,6-二酮
• 英文名称: 2,5-Diazabicyclo<2.2.2>octan-3,6-dion
• 英文别名: 2,5-diazabicyclo<2.2.2>octane-3,6-dione；2,5-Diaza-3,6-dioxo-bicyclo<2.2.2>octan；2,5-Diazabicyclo[2.2.2]octane-3,6-dione
• CAS: 1004-98-4
• 化学式: C₆H₈N₂O₂
• mdl: MFCD18086974
• 分子量: 140.142
• InChiKey: PPSCFPAFAMAAHE-UHFFFAOYSA-N

物化性质

• 熔点：
  272-273 °C
• 沸点：
  554.9±43.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-二氮杂双环[2.2.2]辛烷-3,6-二酮 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 生成 methyl (2S,5S)-6-oxo-5-[(2-phenylacetyl)amino]piperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of (2S,5S)-5-fluoromethylornithine; a potent inhibitor of ornithine aminotransferase

  摘要：

  Only one of the four enantiomers of 5-fluoromethylomithine 1 was an irreversible inhibitor of ornithine aminotransferase. The active enantiomer la was synthesized from diaminoadipic acid 2 with a chemical diastereomeric separation and an enantiomeric resolution by hydrolysis of a phenylacetamide with benzylpenicillinase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00504-6
• 作为产物：
  描述：

  ethyl 5-amino-6-oxopiperidine-2-carboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2,5-二氮杂双环[2.2.2]辛烷-3,6-二酮
  参考文献：
  名称：

  Synthesis of (2S,5S)-5-fluoromethylornithine; a potent inhibitor of ornithine aminotransferase

  摘要：

  Only one of the four enantiomers of 5-fluoromethylomithine 1 was an irreversible inhibitor of ornithine aminotransferase. The active enantiomer la was synthesized from diaminoadipic acid 2 with a chemical diastereomeric separation and an enantiomeric resolution by hydrolysis of a phenylacetamide with benzylpenicillinase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00504-6

文献信息

• [EN] AUTOTAXIN INHIBITORS COMPRISING A HETEROAROMATIC RING-BENZYL-AMIDE-CYCLE CORE<br/>[FR] INHIBITEURS DE L'AUTOTAXINE CONTENANT UN NOYAU À CYCLE BENZYLE-AMIDE CYCLIQUE HÉTÉROAROMATIQUE
  申请人：NOVARTIS AG

  公开号：WO2015008230A1

  公开（公告）日：2015-01-22

  The present invention relates to novel compounds that are autotaxin inhibitors, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in diseases and disorders mediated by autotaxin.

  本发明涉及新型化合物，这些化合物是自体磷脂酶抑制剂，涉及它们的制备方法，含有它们的药物组合物和药物，以及它们在由自体磷脂酶介导的疾病和紊乱中的应用。
• Chirality directed self-assembly. Resolution of 2,5-diazabicyclo[2.2.2]octane-3,6-dione and crystal structures of its racemic and (−) enantiomeric forms
  作者：Marie-Josèphe Brienne、Jacqueline Gabard、Martine Leclercq、Jean-Marie Lehn、Michèle Cesario、Claudine Pascard、Michel Chevé、Gilles Dutruc-Rosset

  DOI：10.1016/0040-4039(94)88270-3

  日期：1994.10

  The chiral bicyclic bis-lactam 1 has been resolved and the crystal structures of the racemate (±)-1 and of enantiomerically pure (−)-1 have been determined. They show that the chiral nature of the substance determines the supramolecular architecture generated by hydrogen bonding self-assembly, giving an infinite zig-zag chain for the racemate and a cyclic tetramer for the enantiomer.

  拆分了手性双环双内酰胺1，并确定了外消旋物（±）-1和对映体纯的（-）- 1的晶体结构。他们表明，该物质的手性决定了氢键自组装产生的超分子结构，外消旋体为无限之字形链，对映体为环状四聚体。
• Diazabicyclooctanes and diazabicycloheptanes
  申请人：Stanford Research Institute

  公开号：US03947445A1

  公开（公告）日：1976-03-30

  Twelve analogs of diethylcarbamazine as prepared by acylation of 3- and 8-methyl-3,8-diazabicyclo[3.2.1]octane, 2-methyl-2,5-diazabicyclo[2.2.2]octane, and 2-methyl-2,5-diazabicyclo [2.2.1]heptane with diethylcarbamyl chloride, ethyl chloroformate, ethyl isocyanate, and cyclohexanecarbonyl chloride. These compounds are formally derived from diethylcarbamazine in possessing two- or one-carbon bridges over the piperazine ring. The compounds have utility as antifilarial agents and as bronchodilators.

  通过对3-和8-甲基-3,8-二氮杂双环[3.2.1]辛烷、2-甲基-2,5-二氮杂双环[2.2.2]辛烷和2-甲基-2,5-二氮杂双环[2.2.1]庚烷进行乙酰化反应，使用乙基氯甲酰胺、氯甲酸乙酯、异氰酸乙酯和环己烷甲酰氯等试剂制备出十二种类似于二乙基氨基甲酸酯的化合物。这些化合物在对哮喘的扩张作用和抗丝虫病治疗方面具有实用价值。这些化合物在皮噻类环上拥有两个或一个碳桥，因此是从二乙基氨基甲酸酯中推导出来的。
• 3-Substituted-8-methyl-3,8-diazabicyclo[3.2.1]octanes
  申请人：Stanford Research Institute

  公开号：US03951980A1

  公开（公告）日：1976-04-20

  Twelve analogs of diethylcarbamazine as prepared by acylation of 3- and 8-methyl-3,8-diazabicyclo[3.2.1]octane, 2-methyl-2,5-diazabicyclo[2.2.2]octane, and 2-methyl-2,5-diazabicyclo[2.2.1]heptane with diethylcarbamyl chloride, ethyl chloroformate, ethyl isocyanate, and cyclohexanecarbonyl chloride. These compounds are formally derived from diethylcarbamazine in possessing two- or one-carbon bridges over the piperazine ring. The compounds have utility as antifilarial agents and as bronchodilators.

  十二种类似二乙基氨基甲酸酯的化合物，是通过将3-和8-甲基-3,8-二氮杂双环[3.2.1]辛烷、2-甲基-2,5-二氮杂双环[2.2.2]辛烷和2-甲基-2,5-二氮杂双环[2.2.1]庚烷与二乙基氨基甲酰氯、乙酰氯、乙酰异氰酸酯和环己烷羰基氯作用制备而成。这些化合物在结构上类似于二乙基氨基甲酸酯，具有在哌嗪环上的两个或一个碳桥。这些化合物可用作抗丝虫药物和支气管扩张剂。
• AUTOTAXIN INHIBITORS
  申请人：BEATTIE David

  公开号：US20160184318A1

  公开（公告）日：2016-06-30

  The present invention relates to novel compounds that are autotaxin inhibitors, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in diseases and disorders mediated by autotaxin.

  本发明涉及新型的自体磷脂酰肌醇酰化酶抑制剂化合物，其制备方法，包含它们的药物组合物和药物以及它们在由自体磷脂酰肌醇酰化酶介导的疾病和障碍中的应用。