1,4-diacetyl-2,3-diphenyl-1,4,5,6-tetrahydropyrazine | 32174-85-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,4-diacetyl-2,3-diphenyl-1,4,5,6-tetrahydropyrazine
• 英文别名: 2,3-Diphenyl-1,4-diacetyl-1,4,5,6-tetrahydropyrazin；1,4-diacetyl-5,6-diphenyl-1,2,3,4-tetrahydro-pyrazine；1,4-Diacetyl-5,6-diphenyl-1,2,3,4-tetrahydro-pyrazin；1-(4-Acetyl-5,6-diphenyl-2,3-dihydropyrazin-1-yl)ethanone；1-(4-acetyl-5,6-diphenyl-2,3-dihydropyrazin-1-yl)ethanone
• CAS: 32174-85-9
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: DOJZGEJBJXVOTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-diacetyl-2,3-diphenyl-1,4,5,6-tetrahydropyrazine 在 二甲基二环氧乙烷 作用下， 以 氘代氯仿 、 丙酮 为溶剂， 生成 3-Chloro-benzenecarboperoxoic acid 1,4-diacetyl-3-hydroxy-2,3-diphenyl-piperazin-2-yl ester
  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：

  5,6-二苯基-2,3-二羟基吡嗪 生成 1,4-diacetyl-2,3-diphenyl-1,4,5,6-tetrahydropyrazine
  参考文献：
  名称：

  Synthesis of the 1,4-dihydropyrazine ring system. Stable 8.pi.-electron heterocycle

  摘要：

  DOI：

  10.1021/jo00825a004

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.
• Synthesis of the 1,4-dihydropyrazine ring system. Stable 8.pi.-electron heterocycle
  作者：Frank W. Fowler、Shue-Jen Chen

  DOI：10.1021/jo00825a004

  日期：1971.12