4,6-dichloro-2-ethyl-1-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one | 138610-79-4

• 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-ethyl-1-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one
• 英文别名: 4,6-dichloro-2-ethyl-1-phenyl-2,5-diazabicyclo[2.2.2]oct-5-en-3-one
• CAS: 138610-79-4
• 化学式: C₁₄H₁₄Cl₂N₂O
• 分子量: 297.184
• InChiKey: ROQNNZSFGMGTKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 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-ethyl-1-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one 在 palladium on activated charcoal 三乙烯二胺 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以58%的产率得到4-chloro-2-ethyl-1-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-dichloro-1-ethyl-6-phenyl-2(1H)-pyrazinone 以 甲苯 为溶剂， 110.0 ℃ 、2.53 MPa 条件下， 反应 48.0h， 生成 4,6-dichloro-2-ethyl-1-phenyl-2,5-diazabicyclo<2.2.2>oct-5-en-3-one
  参考文献：
  名称：

  Cycloadducts of ethene with 2(1H)-pyrazinones and their conversion into 2,5-diazabicyclo[2.2.2]octane-3,6-diones.

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)96214-3

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.
• 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.