8-benzoyl-2-(4-tolyl)-3,4-dihydropyrrolo[1,2-a]-pyrazine-1,6,7(2H)-trione | 1448152-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 8-benzoyl-2-(4-tolyl)-3,4-dihydropyrrolo[1,2-a]-pyrazine-1,6,7(2H)-trione
• 英文别名: 8-benzoyl-2-(4-methylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-1,6,7-trione
• CAS: 1448152-51-9
• 化学式: C₂₁H₁₆N₂O₄
• 分子量: 360.369
• InChiKey: UAJJCYFBKJOGEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-benzoyl-2-(4-tolyl)-3,4-dihydropyrrolo[1,2-a]-pyrazine-1,6,7(2H)-trione 在 水 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以93%的产率得到(E)-8a-hydroxy-8-[hydroxy(phenyl)methylidene]-2-(4-tolyl)tetrahydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-trione
  参考文献：
  名称：

  Synthesis of 8-aroylpyrrolo[1,2-a]pyrazine-1,6,7(2H)-triones and their reaction with water. New analogs of cyclic dipeptides

  摘要：

  2-Aryl-8-aroyl-3,4-dihydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-triones prepared from (Z)-1-aryl-3-(2-aryl-2-oxoethylidene)piperazin-2-ones and oxalyl chloride react with water to afford (E)-8D degrees-hydroxy-2-aryl-8-[aryl(hydroxy)methylene]tetrahydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-triones. The crystal and molecular structure of 8-benzoyl-2-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-trione and (E)-8D degrees-hydroxy-8-[hydroxy(phenyl)methylene]-2-phenyltetrahydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-trione were studied by X-ray diffraction analysis.

  DOI：

  10.1134/s1070428015110123
• 作为产物：
  描述：

  (Z)-8-[hydroxy(phenyl)methylidene]-2-(4-methylphenyl)-8a-chlorotetrahydropyrrolo[1,2-a]pyrazine-1,6,7(2H)-trione 以 甲苯 为溶剂， 反应 2.0h， 以97%的产率得到8-benzoyl-2-(4-tolyl)-3,4-dihydropyrrolo[1,2-a]-pyrazine-1,6,7(2H)-trione
  参考文献：
  名称：

  Synthesis of 8a-Chlorotetrahydropyrrolo[1,2-H]pyrazine-1,6,7-(2H)-triones from 3-Methylidenepiperazin-2-ones and Oxalyl Chloride

  摘要：

  (Z)-1-Aryl-3-(2-aryl-2-oxoethylidene)piperazin-2-ones react with oxalyl chloride at cooling with the formation of (Z)-2-aryl-8-[hydroxy(aryl)methylidene]-8D degrees-chlorotetrahydropyrrolD 3/4 [1,2-a]pyrazine-1,6,7(2H)-triones. At heating HCl is eliminated from them to produce 8-aroyl-3,4-dihydropyrrolD 3/4 [1,2-D degrees]pyrazine- 1,6,7(2H)-triones.

  DOI：

  10.1134/s1070428018050263

文献信息

• Reaction of pyrrolo[1,2-a]pyrazinetriones with o-phenylenediamine. Synthesis of angular benzo[b]pyrazino[1′,2′: 1,2]pyrrolo[2,3-e][1,4]diazepines
  作者：A. V. Chervyakov、A. N. Maslivets

  DOI：10.1134/s1070428016040291

  日期：2016.4

  formation of substituted benzo[b]pyrrolo[2,3-e][1,4]diazepines [3]. The first step in the reaction of 3-pivaloylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with o-phenylenediamine is addition of the amino group in the latter to C, and subsequent opening of the pyrrole ring and heterocyclization lead to 3-(quinoxalin-2-ylmethyl)quinoxalin-2-one derivatives [4]. We previously synthesized new hetareno[e]pyrrole2

  已知通过 N-C 键与氮杂环稠合的 4-酰基取代的 1H-吡咯-2,3-二酮可通过三种途径与邻苯二胺反应。3-Aroyland 3-heteroaroylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones（1H-pyrrole-2,3-diones 通过 N–C 键与 1,4-苯并恶嗪片段）与邻苯二胺反应，首先将氨基加到 C 上，打开恶嗪和吡咯环，然后杂环化为 quinoxalin-2-one 衍生物 [1, 2]。3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4-triones（1H-pyrrole-2,3-diones 通过 N-C 键与喹喔啉片段融合）也通过初始添加与邻苯二胺反应氨基到 C，但接下来是分子内环化，涉及芳酰基羰基，形成取代的苯并 [b] 吡咯并 [2,3-e][1,4] 二氮杂 [3]。3-pivaloylpyrrolo[1
• Synthesis of pyrrolo[1,2-a]pyrazine-1,6,7-triones from 3-methylidenepiperazin-2-ones and oxalyl chloride
  作者：A. V. Chervyakov、A. N. Maslivets

  DOI：10.1134/s1070428013060286

  日期：2013.6