1-(4-Acetyl-2,3-dimethylquinoxalin-1-yl)ethanone | 171255-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(4-Acetyl-2,3-dimethylquinoxalin-1-yl)ethanone
• 英文别名: 1-(4-acetyl-2,3-dimethylquinoxalin-1-yl)ethanone
• CAS: 171255-46-2
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: NUWMMOJWSKGVGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Acetyl-2,3-dimethylquinoxalin-1-yl)ethanone 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 生成 1-(2-Acetyl-1a,7a-dimethyloxireno[2,3-b]quinoxalin-7-yl)ethanone
  参考文献：
  名称：

  Chemiluminescence of the Labile 1,2-Dioxetanes and Epoxides Produced in the Oxidation of N-Acetylated Dihydro- and Tetrahydropyrazines by Singlet Oxygen, Dimethyldioxirane, and m-Chloroperoxybenzoic Acid

  摘要：

  The oxidation of the N-acylated pyrazine derivatives 1a,b gave the pyrazine-type dioxetanes 2a,b, which for the first time were isolated and characterized. The halflives of the thermal decomposition of these labile dioxetanes at 20 degrees C were determined by chemiluminescence measurements to be 80 +/- 2 (2a) and 18 +/- 1 min (2b). Upon thermolysis, the dioxetanes 2a,b decomposed quantitatively to the corresponding C-2-C-3 cleavage products 3a,b. The deoxygenation of the dioxetanes 2a,b by dimethyl sulfide yielded predominantly the novel pyrazine-type epoxides 4a,b, accompanied by some dioxetane decomposition product 3a,b. Upon thermolysis, the epoxide 4b decomposed to the benzodiazine 5b and the enone 6b. Dimethyldioxirane oxidation of the pyrazine derivatives 1a,b afforded the epoxides 4a,b, while treatment with an excess of m-chloroperoxybenzoic acid (m-CPBA) led to the C-2-C-3 cleavage products 3a,b with intense light emission by way of the intermediary peroxy esters 8.

  DOI：

  10.1021/ja00143a011
• 作为产物：
  描述：

  2,3-二甲基喹喔啉 、 乙酸酐 在 锌 作用下， 以68%的产率得到1-(4-Acetyl-2,3-dimethylquinoxalin-1-yl)ethanone
  参考文献：
  名称：

  Chemiluminescence of the Labile 1,2-Dioxetanes and Epoxides Produced in the Oxidation of N-Acetylated Dihydro- and Tetrahydropyrazines by Singlet Oxygen, Dimethyldioxirane, and m-Chloroperoxybenzoic Acid

  摘要：

  The oxidation of the N-acylated pyrazine derivatives 1a,b gave the pyrazine-type dioxetanes 2a,b, which for the first time were isolated and characterized. The halflives of the thermal decomposition of these labile dioxetanes at 20 degrees C were determined by chemiluminescence measurements to be 80 +/- 2 (2a) and 18 +/- 1 min (2b). Upon thermolysis, the dioxetanes 2a,b decomposed quantitatively to the corresponding C-2-C-3 cleavage products 3a,b. The deoxygenation of the dioxetanes 2a,b by dimethyl sulfide yielded predominantly the novel pyrazine-type epoxides 4a,b, accompanied by some dioxetane decomposition product 3a,b. Upon thermolysis, the epoxide 4b decomposed to the benzodiazine 5b and the enone 6b. Dimethyldioxirane oxidation of the pyrazine derivatives 1a,b afforded the epoxides 4a,b, while treatment with an excess of m-chloroperoxybenzoic acid (m-CPBA) led to the C-2-C-3 cleavage products 3a,b with intense light emission by way of the intermediary peroxy esters 8.

  DOI：

  10.1021/ja00143a011

文献信息

• Chemiluminescence of the Labile 1,2-Dioxetanes and Epoxides Produced in the Oxidation of N-Acetylated Dihydro- and Tetrahydropyrazines by Singlet Oxygen, Dimethyldioxirane, and m-Chloroperoxybenzoic Acid
  作者：Waldemar Adam、Michael Ahrweiler、Pavel Vliek

  DOI：10.1021/ja00143a011

  日期：1995.9

  The oxidation of the N-acylated pyrazine derivatives 1a,b gave the pyrazine-type dioxetanes 2a,b, which for the first time were isolated and characterized. The halflives of the thermal decomposition of these labile dioxetanes at 20 degrees C were determined by chemiluminescence measurements to be 80 +/- 2 (2a) and 18 +/- 1 min (2b). Upon thermolysis, the dioxetanes 2a,b decomposed quantitatively to the corresponding C-2-C-3 cleavage products 3a,b. The deoxygenation of the dioxetanes 2a,b by dimethyl sulfide yielded predominantly the novel pyrazine-type epoxides 4a,b, accompanied by some dioxetane decomposition product 3a,b. Upon thermolysis, the epoxide 4b decomposed to the benzodiazine 5b and the enone 6b. Dimethyldioxirane oxidation of the pyrazine derivatives 1a,b afforded the epoxides 4a,b, while treatment with an excess of m-chloroperoxybenzoic acid (m-CPBA) led to the C-2-C-3 cleavage products 3a,b with intense light emission by way of the intermediary peroxy esters 8.