4,6-Dichloro-2-phenethyl-2,5-diaza-bicyclo[2.2.2]oct-5-en-3-one | 139268-45-4

• 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
• 英文名称: 4,6-Dichloro-2-phenethyl-2,5-diaza-bicyclo[2.2.2]oct-5-en-3-one
• 英文别名: 4,6-dichloro-2-(2-phenylethyl)-2,5-diazabicyclo[2.2.2]oct-5-en-3-one
• CAS: 139268-45-4
• 化学式: C₁₄H₁₄Cl₂N₂O
• 分子量: 297.184
• InChiKey: NTVWQQPPJLUTTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 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-phenethyl-2,5-diaza-bicyclo[2.2.2]oct-5-en-3-one 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以76%的产率得到4-chloro-2-phenethyl-2,5-diazabicyclo<2.2.2>octane-3,6-dione
  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
• 作为产物：
  描述：

  乙烯 、 3,5-dichloro-1-phenethyl-2(1H)-pyrazinone 以 甲苯 为溶剂， 110.0 ℃ 、2.53 MPa 条件下， 反应 18.0h， 生成 4,6-Dichloro-2-phenethyl-2,5-diaza-bicyclo[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 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.