4,6-dichloro-2-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one | 138610-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4,6-dichloro-2-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one
• 英文别名: 4,6-dichloro-2-phenyl-2,5-diazabicyclo[2.2.2]oct-5-en-3-one
• CAS: 138610-78-3
• 化学式: C₁₂H₁₀Cl₂N₂O
• 分子量: 269.13
• InChiKey: PEDQYOYASGHRCP-UHFFFAOYSA-N

物化性质

• 沸点：
  479.8±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-2-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one 在 palladium on activated charcoal 三氯化铝 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 生成 4-chloro-6-(4-methoxyphenyl)-2-phenyl-2,5-diazabicyclo<2.2.2>octan-3-one
  参考文献：
  名称：

  Cycloadducts of ethene with 2(1H)-pyrazinones functionalisation and reduction to 2,5-diazabicyclo[2.2.2]octan-3-ones.

  摘要：

  The title compounds 4 were prepared via Diels-Alder reaction of 3,5-dichloro-2(1H)-pyrazinones 1 with ethene, followed by catalytic reduction of the iminochloride group generated in the cycloadducts 2. Substitution of the iminochloride group with various nucleophiles afforded the 6-functionalised analogues of 2. Their reduction can lead to 6-substituted derivatives of compounds 4. One example is given.

  DOI：

  10.1016/s0040-4020(01)96215-5
• 作为产物：
  描述：

  乙烯 、 3,5-二氯-1-苯基吡嗪-2(1H)-酮 以 邻二氯苯 为溶剂， 反应 2.33h， 以89%的产率得到4,6-dichloro-2-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one
  参考文献：
  名称：

  2（1H）-吡嗪酮在离子液体掺杂溶剂中的高速微波促进异Diels-Alder反应。

  摘要：

  在受控的微波辐射下，研究了一系列功能化的2（1H）-吡嗪酮中的分子间和分子内异Diels-Alder反应。利用1,2-二氯乙烷和热稳定的离子液体的组合，或1,2-二氯苯作为反应介质，可以在密封管中高效地进行环加成反应。在所有情况下，与热加热相比，观察到使用微波闪蒸加热显着提高了速率。

  DOI：

  10.1021/jo0263216

文献信息

• Cycloadducts of ethene with 2(1H)-pyrazinones and their conversion into 2,5-diazabicyclo[2.2.2]octane-3,6-diones.
  作者：Patrick K. Loosen、Mayoka G. Tutonda、Masoumeh F. Khorasani、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96214-3

  日期：1991.11

  Cycloaddition of variously substituted 2(1H)-pyrazinones with ethene and subsequent hydrolysis of the adducts 2 provides a general and efficient route to the title compounds 3. Compound 3m was used as a building block for a structural analogue of gliotoxin.
• High-Speed Microwave-Promoted Hetero-Diels−Alder Reactions of 2(1<i>H</i>)-Pyrazinones in Ionic Liquid Doped Solvents
  作者：Erik Van der Eycken、Prasad Appukkuttan、Wim De Borggraeve、Wim Dehaen、Doris Dallinger、C. Oliver Kappe

  DOI：10.1021/jo0263216

  日期：2002.11.1

  hetero-Diels-Alder reactions in a series of functionalized 2(1H)-pyrazinones were investigated under controlled microwave irradiation. The cycloaddition reactions were efficiently performed in sealed tubes, utilizing either a combination of 1,2-dichloroethane and a thermally stable ionic liquid, or 1,2-dichlorobenzene as reaction medium. In all cases, a significant rate-enhancement using microwave flash heating

  在受控的微波辐射下，研究了一系列功能化的2（1H）-吡嗪酮中的分子间和分子内异Diels-Alder反应。利用1,2-二氯乙烷和热稳定的离子液体的组合，或1,2-二氯苯作为反应介质，可以在密封管中高效地进行环加成反应。在所有情况下，与热加热相比，观察到使用微波闪蒸加热显着提高了速率。
• Cycloadducts of ethene with 2(1H)-pyrazinones functionalisation and reduction to 2,5-diazabicyclo[2.2.2]octan-3-ones.
  作者：Patrick K. Loosen、Masoumeh F. Khorasani、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96215-5

  日期：1991.11

  The title compounds 4 were prepared via Diels-Alder reaction of 3,5-dichloro-2(1H)-pyrazinones 1 with ethene, followed by catalytic reduction of the iminochloride group generated in the cycloadducts 2. Substitution of the iminochloride group with various nucleophiles afforded the 6-functionalised analogues of 2. Their reduction can lead to 6-substituted derivatives of compounds 4. One example is given.